Jacques Anquetil

2.4.1. 1958: Année Terrible

In 1958, Anquetil started his season slowly. He won the time trial stage at Paris-Nice in March but only finished tenth overall, the same position he achieved at Milan-San Remo a couple of days later. After finishing twelfth at the Critérium National, he targeted Paris-Roubaix, a race he felt suited him. Still 124 mile ^{(200 km)} from the finish, he launched an attack, creating a 17-rider lead group, which quickly dwindled to just four due to Anquetil's relentless pace. However, the Belgian teams in the peloton never allowed the gap to exceed four minutes. Although Anquetil managed to rejoin the lead group after a puncture 8.1 mile ^{(13 km)} from the finish, the group was eventually caught 2.5 mile ^{(4 km)} before the line. His failure to win at Roubaix was noted by the public, as it was the first time he had started a classics race with the explicit intention of winning. Anquetil bounced back by winning the Four Days of Dunkirk. In preparation for the Tour de France, he then finished eighth at the national championships.

As the defending champion, Anquetil was the French team's top choice for the Tour de France. However, Bidot could not exclude three-time winner Bobet, leaving the team with two captains. Anquetil agreed but insisted that Bobet's close ally Géminiani be left off the squad. Bidot conceded, and as Bobet did not support Géminiani, their friendship became heavily strained. Géminiani entered the Tour as the leader of the Centre-Midi regional team and seized every opportunity to attack the main French squad. After an uneventful start, Géminiani attacked on stage 6, gaining ten minutes on Anquetil. Two days later, during the Tour's first time trial, Anquetil suffered another blow when Charly Gaul, typically known more as a climber than a time trialist, managed to beat Anquetil in his favored discipline, albeit by just seven seconds. On stage 18, a mountain time trial up Mont Ventoux, Anquetil lost over four minutes to Gaul. While he had predicted such a result before the Tour, as the climb suited Gaul more, it was still a significant loss given the time Anquetil had already conceded. Géminiani, meanwhile, did enough to secure the yellow jersey and gained more time on the following stage due to an untimely mechanical issue for Gaul. Heading into stage 21 to Aix-les-Bains, Géminiani led the overall standings, Anquetil was third, 7:57 minutes behind, while Gaul was fifth, over 15 minutes adrift. The stage featured five climbs, on the second of which Gaul attacked in rainy and cold conditions. Anquetil followed, only two minutes behind Gaul at the foot of the next climb, the Col de Porte. The weather then affected Anquetil, who had chosen to wear a light silk jersey instead of wool. He lost 22 minutes by the end of the stage and developed a chest infection. Géminiani fared little better, losing 15 minutes to Gaul, who would go on to win the Tour after winning the final time trial. Even with his infection, Anquetil decided to start the following stage to help the French team win the team classification, but after coughing up blood, he was hospitalized with a 105.08000000000001 °F ^{(40.6 °C)} fever and forced to abandon.

Anquetil took time to recover from his infection. He later described this period as the lowest point in his career, even contemplating retirement, but ultimately continued. The illness still hampered his efforts at the World Championships in Reims, where he abandoned. He recovered to win three end-of-season time trials: the Grands Prix in Geneva and Lugano, and the Grand Prix des Nations for the sixth consecutive time. He then finished twelfth at both Paris-Tours and the Giro di Lombardia before ending the road season with a second-place finish at the Trofeo Baracchi. On the track, Anquetil, Darrigade, and Teruzzi successfully defended their title at the Paris Six-Days, concluding the year at the Vélodrome d'Hiver for the last time the event was held there. Anquetil's biographer Paul Howard later described 1958 as his année terrible ("terrible year").

2.4.2. 1959: Failed Attempt at the Giro-Tour Double

By early 1959, Roger Rivière had emerged as a serious challenger to Anquetil. Rivière had not only beaten Anquetil to become World Champion in the individual pursuit but also broke Baldini's hour record and later improved it again, becoming the first man to cover over 29 mile ^{(47 km)} in an hour. The two riders first faced each other on the road at the 1959 Paris-Nice, which that year was called Paris-Nice-Rome, ending in Rome. Neither rider won, and Rivière finished higher in the overall classification, but Anquetil's teammate Jean Graczyk took the victory, and Anquetil was faster in the time trial.

For 1959, Anquetil set a goal to emulate his idol Fausto Coppi by winning both the Giro d'Italia and the Tour de France in the same year. Gaul, who had previously won the Giro in 1956, was also competing. Anquetil started the Giro strongly, taking the race leader's pink jersey after a short time trial on stage 2. He lost his lead to Gaul the following day on a hilltop finish. Gaul increased his advantage on stage 7 by winning the mountain time trial up Mount Vesuvius, extending his lead over second-placed Anquetil to 2:19 minutes. Anquetil managed to gain back 22 seconds on Gaul the next day in another time trial. During stage 12, which featured three ascents of Monte Titano in San Marino, he managed to distance Gaul, gaining one-and-a-half minutes and reducing his deficit to just 34 seconds. On stage 15, Anquetil escaped with several other riders on a downhill section and gained another two-and-a-half minutes on Gaul, reclaiming the pink jersey. While leading the race, Anquetil then won the stage 19 time trial to Susa. Riding at an average speed of 30 mph ^{(47.713 km/h)} (faster than Rivière's hour record speed), Anquetil still only gained 2:01 minutes on Gaul, who had started his effort one-and-a-half minutes ahead of Anquetil and had clung on to limit his losses after Anquetil passed him. After the time trial, Anquetil led Gaul by 3:49 minutes in the overall standings. The decisive stage came on stage 21 to Courmayeur, where Gaul attacked on the Col du Petit-Saint-Bernard and ultimately arrived at the stage finish almost ten minutes ahead of Anquetil to secure overall victory. Anquetil finished the Giro in second place, 6:12 minutes behind Gaul.

For the Tour de France, the French national team started with four potential contenders for overall victory: Anquetil, Bobet, Géminiani, and Rivière. While the latter two were riding on the same trade team and got along well, there was little sympathy and cooperation among the other riders. Bobet retired from what would be his last Tour on top of the Col de l'Iseran, while Géminiani was significantly weaker than the previous year and posed no threat for overall victory. The French team's main challengers came from Gaul, Spain's Federico Bahamontes, Italian Ercole Baldini, and Henry Anglade, a Frenchman riding on the Centre/Midi regional team. The first notable stage for the general classification was the stage 6 time trial, won by Rivière, 21 seconds ahead of Baldini and almost a minute faster than Anquetil. The following day, Anglade was part of a breakaway that gained nearly five minutes on the rest of the field. On stage 13, Anglade won ahead of Anquetil, with Baldini and Bahamontes also in the lead group. Gaul struggled on the stage and lost twenty minutes, effectively ruling him out of contention. Anglade was now second in the overall standings, over three minutes ahead of Baldini, Bahamontes, and Anquetil, while Rivière was over six minutes behind Anglade. Two days later, Bahamontes won the mountain time trial up the Puy de Dôme, taking over three minutes from Anglade's lead. Anquetil was now sixth in the standings, over five minutes behind second-placed Bahamontes. On stage 17 in the Alps, Bahamontes and Gaul escaped together; Gaul took the stage win while Bahamontes moved into the race lead, finishing three-and-a-half minutes ahead of the other challengers. The next stage was the decisive one, featuring several high mountain climbs. Following the Col de l'Iseran, Anquetil and Rivière found themselves in a lead group, having distanced Bahamontes and Gaul, but then allowed them to catch back on. On the descent of the following climb, the Col du Petit-Saint-Bernard, Anglade, Baldini, and Gaul attacked. Anquetil and Rivière both assisted Bahamontes in regaining contact with the others. Baldini would win the stage while Bahamontes remained in the lead, 4:04 minutes ahead of Anglade, who lost another minute the following day. In the time trial on the penultimate stage to Dijon, Rivière again won ahead of Anquetil, beating him by 1:38 minutes, while Bahamontes sealed overall victory. As the French riders entered the Parc des Princes during the final stage, they were booed by the crowd, who felt that Anquetil and Rivière had colluded with Bahamontes against their fellow Frenchman, Anglade. This decision might have been influenced by the fact that if another French rider had won the Tour, Anquetil's market value for participation money in the lucrative post-Tour criteriums would have been less. Anquetil made no secret that he embraced the hostile reaction of the crowd, later naming a boat he owned Sifflets '59 ("The Whistles of '59"). Anquetil eventually finished the Tour third overall, 17 seconds ahead of fourth-placed Rivière.

At the World Championships in Zandvoort, Anquetil finished ninth as his friend Darrigade won the title. In early September, he won the prestigious Critérium des As, a race run behind dernys. Anquetil ended his season with victories at the Grand Prix Martini and Grand Prix de Lugano time trials, but for the first time since his first victory in 1953, he did not compete in the Grand Prix des Nations, which was won by Aldo Moser ahead of Rivière. At the Trofeo Baracchi, Anquetil, paired with Darrigade, finished only third after missing the start time by over a minute, and they were also outridden by the pairing of Moser and Baldini.

2.5.1. 1960: Giro d'Italia Success

Following two years without a major stage race victory and with Rivière proving his match in time trials, Anquetil's star seemed to be fading at the beginning of 1960. Not wanting to share leadership of the French team with Rivière, Anquetil chose to focus solely on the Giro d'Italia that year. At Paris-Nice, in the team time trial on stage 2, Anquetil, who suffered mechanical issues, was dropped by his teammates and lost four-and-a-half minutes on his principal rivals. On stage 4, a large breakaway got clear, and Anquetil's team decided not to organize a chase. This allowed the leading group to finish over 23 minutes ahead of the field, making it virtually impossible for anyone not in it to compete for overall victory. Anquetil's poor form was further highlighted when he finished only fourth in the time trial on stage 6b, and he retired the following day. He then finished third at the Critérium National before coming in fourteenth at the Tour of Flanders.

In the first time trial of the Giro d'Italia, Anquetil finished second but then capitalized on a breakaway he was part of on stage 3 to take the overall lead. Anquetil then led the chase to Jos Hoevenaers, who had been part of a breakaway on stage 6. In the long time trial of the race on stage 14, Anquetil retook the lead, finishing 1:27 minutes ahead of Baldini and over six minutes on Gaul. His speed was so fast that if the organizers had applied the usual rules, 70 riders would have missed the time cut; however, the rules were loosened, and only two riders were eliminated. Ahead of the final mountain stages, Anquetil now led Nencini by 3:40 minutes, with Gaul in fifth, 7:32 minutes behind. Stage 20 included the Gavia Pass for the first time in the race's history. On the ascent, Nencini managed to establish a gap on Anquetil after the latter had a flat tire. More punctures and three bike changes followed on the dangerous descent, jeopardizing Anquetil's race lead. He teamed up with Agostino Coletto, whom he offered money to help him in the chase effort, to limit his losses. At the finish in Bormio, Gaul won ahead of Nencini, with Anquetil losing only 2:34 minutes and retaining the pink jersey by 28 seconds. Following a ceremonial final stage, Anquetil arrived in Milan as the winner of the Giro for the first time.

In Anquetil's absence, Rivière competed in the 1960 Tour de France as leader of the French team and was well placed when, on stage 14, he crashed while trying to follow Nencini on a steep descent. He fell 33 ft ^{(10 m)} down a ravine and broke two vertebrae, immediately ending his career. The great rivalry with Anquetil thus ended abruptly. Paul Howard later wrote that with Rivière's accident, "by late 1960 Anquetil was temporarily free from a serious adversary, at least within French cycling circles."

At the World Championships in East Germany, Anquetil arrived with little preparation but still managed to finish ninth. Another strong time trial performance followed at the Grand Prix de Lugano, where Anquetil was so fast that second-placed rider Gilbert Desmet owed his position to the fact that Anquetil overtook him and he followed him into the finish. He followed this up with another victory at the Critérium des As, breaking the record speed in the process. Having attacked 6.2 mile ^{(10 km)} into the race to test his legs, Anquetil decided he felt so good that he did not slow down and rode alone until the finish.

2.5.2. 1961: Tour de France Return

In early 1961, Anquetil took victory at Paris-Nice. At the Critérium National, he attacked with 0.9 mile ^{(1.5 km)} left to go and won ahead of Darrigade, who had switched teams to Alcyon-Leroux. It was Anquetil's first ever victory at a one-day road race. He then competed in the Tour de Romandie, winning the time trial and finishing tenth overall, in preparation for the Giro d'Italia.

At the Giro, Anquetil won the time trial on stage 9 and gained the pink jersey the following day, when he was part of a breakaway that reached the finish ahead of previous leader Guillaume van Tongerloo. On stage 14, a seven-rider breakaway got away, which included Arnaldo Pambianco, who was third overall. At the finish, they had a 1:42 minute advantage on the peloton containing Anquetil, putting Pambianco into the lead. Anquetil then lost another twenty seconds on stage 17 before the race reached the high mountains. On the decisive stage 20, which featured the climbs of the Penser Joch and the Stelvio Pass, Gaul won two minutes ahead of Pambianco, with Anquetil losing another three minutes (two of which were in time bonuses). Therefore, Pambianco won the Giro, 3:45 minutes ahead of Anquetil.

At the National Championship race before the Tour, Anquetil finished fourth, with the title going to Raymond Poulidor, who had earlier in the year won Milan-San Remo. Poulidor would emerge as Anquetil's new main rival, but was left out of the French team for the upcoming Tour de France as his team manager Antonin Magne did not want him to have to work for Anquetil. The Tour began in Anquetil's hometown of Rouen, and before the start, he announced that he planned to hold the race lead from the first day until the end. There were two stages run on the first day: a road stage to Versailles in the morning and then a time trial in the afternoon, with the yellow jersey only being awarded at the end of the day. Anquetil already got in the winning breakaway on the first stage, won by Darrigade, and then in the afternoon, he won the time trial by over three minutes from the rider in second place to move into the overall lead. Over the course of the race, Anquetil rode very passively, only chasing down attacks and limiting his losses, but never going on the attack himself. This led to a race that was considered dull by the public, with sales numbers of the organizing newspaper L'Equipe decreasing as the Tour progressed. Anquetil won the time trial on stage 19 to effectively seal his second Tour de France victory, finishing the course almost three minutes faster than second-placed Gaul. On the final stage into Paris, he attacked together with teammate Robert Cazala, who won the stage. Guido Carlesi used the same breakaway to distance Gaul and take over second place. Anquetil's winning margin over him was 12:14 minutes. Due to what the spectators considered a lack of excitement during the race, Anquetil was booed when they arrived at the Parc des Princes.

Following the Tour, Anquetil competed at the World Championships in Bern, finishing in the lead group in 13th place. He then rode the Grand Prix des Nations for the first time since 1958, taking victory in record time and beating second-placed Desmet by over nine minutes. Following victory at the Grand Prix de Lugano, he managed only fifth place at the Trofeo Baracchi, partnered by Michel Stolker, his worst position at the event during his career. Nevertheless, at the end of the season he was honored with the Super Prestige Pernod for the first time, an award given to the best rider of the year based on points given for high positions in prestigious races.

2.5.3. 1962: Third Tour de France Victory

For the new season in 1962, Anquetil's team Helyett folded and merged with the Saint-Raphaël team, whose sporting director was Géminiani, Anquetil's former rival, who had since retired. His early season results were not good, as he had to retire from both Genoa-Nice and Paris-Nice. Anquetil had set himself the goal to become the first rider to have won all three of cycling's Grand Tours, which meant that for 1962, he targeted the Vuelta a España. Here, he had to share team leadership with Rudi Altig. The race came down to the time trial on stage 15, which Altig won decisively. Anquetil then dropped out of the race following the stage, only to be diagnosed with viral hepatitis once back in France. Altig eventually won the Vuelta. Against the advice of his doctor, who felt that the illness had weakened Anquetil too much, he then raced in the Critérium du Dauphiné Libéré in preparation for the Tour. He suffered during the fifth stage, where he lost 17 minutes, but managed to finish the race in 12th place overall.

For the 1962 Tour de France, the organizers dropped the provisions of national teams and allowed the riders to compete in trade teams, meaning that Anquetil rode for Saint-Raphaël. Poulidor was considered his main competition along with reigning World Champion Rik van Looy; both were riding their first Tour. A break within the peloton on the first stage, won by Altig, saw Poulidor lose almost eight minutes. Anquetil won the stage 8b time trial and moved into 12th place in the general classification, behind a number of riders who had been in an earlier breakaway but were not considered threats for overall victory. On stage 11, the first in the Pyrenees, van Looy was brought down when a motorbike caused a crash, leading him to abandon. After stage 12, also in the high mountains, Anquetil moved up into sixth place. The following day was a mountain time trial to Superbagnères. Anquetil finished the day third, behind stage winner Bahamontes and Jef Planckaert, the surprise of the Tour, who moved into the race lead, with Anquetil in fourth, 1:08 minutes behind. On stage 19, Poulidor escaped and went on to win the stage, while Anquetil finished with Planckaert, which left their time difference intact. However, Anquetil had moved up to second and Poulidor up to third. In the 42 mile ^{(68 km)} time trial on stage 20 to Lyon, Anquetil won with ease, catching Poulidor for three minutes at the half-way mark of the course and beating Planckaert by 5:19 minutes. This gave Anquetil a record-equalling third Tour victory, 4:59 minutes ahead of Planckaert, who showed sportsmanship when he did not attack Anquetil when the latter suffered a crash on the final day into Paris. After the Tour, it was discovered that Anquetil had ridden the entire event with a tapeworm.

While recovering from the worm, Anquetil placed only fifteenth at the World Championships in Salò, won by his friend and teammate Jean Stablinski. Still weakened, he then skipped most of the late-season time trials, except for the Trofeo Baracchi, which he attended together with Altig. Not having prepared well for the event, Anquetil suffered from the beginning and was unable to take turns at the front, forced to stay in Altig's slipstream and at some points suffering the humiliation of Altig having to push him in order to keep up. When they reached the finish, their time was taken at the entrance of the velodrome. As they entered the arena, Anquetil was unable to take the sharp right turn onto the track, drove onto the grass, and crashed into a crowd of spectators. The pair had won the event, in record time, but Anquetil was brought into hospital, his face covered in blood, while Altig took the victory lap on his own. Feeling humiliated by the experience, Anquetil prepared well for a similar two-man time trial event two weeks later in Altig's home country, in Baden-Baden. This time, it was Anquetil who set a high pace which Altig had a hard time following.

2.5.4. 1963: Vuelta-Tour Double

Early in 1963, Anquetil won Paris-Nice and the Critérium National in preparation for another attempt at the Vuelta. He lined up at the 1963 Vuelta a España in good shape. He won the stage 1b time trial on the first afternoon by 2:51 minutes on the second-placed rider, including the time bonus, he already held over three minutes advantage on his rivals. Anquetil's team managed to neutralize all the attacks during the difficult first week. The remaining stages were mostly flat and suited Anquetil. Even though he only finished second on the stage 12b time trial to Tarragona, suffering from stomach cramps, he eventually won the Vuelta easily, beating José Martín Colmenarejo by 3:06 minutes. With his victory, he became the first rider to have won all the Grand Tours.

To prepare for the Tour, Anquetil competed in the Critérium du Dauphiné Libéré, where he won the time trial and the general classification. Thereafter, he helped Stablinski to victory at the National Championships, himself finishing third. The Tour de France became a fight between Anquetil and Bahamontes, who gained time when he got into a breakaway on the first stage. After winning the stage 6b time trial, Anquetil moved up into seventh place overall, behind a number of riders who had been in earlier breakaways, but over a minute ahead of Bahamontes and Poulidor. On stage 10, he managed to stay with Bahamontes and outsprinted him at the finish, gaining his first-ever victory on a mountain stage. On stage 17, Anquetil and Géminiani used a ruse, pretending to suffer a broken chain, to allow Anquetil to switch to a lighter bike for the ascent of the Col de la Forclaz, enabling him to stay with Bahamontes on the steep climb and again outsprint him at the finish. He had therefore moved into the race lead, extending his advantage in the final time trial. His eventual winning margin over Bahamontes was 3:35 minutes as he became the first rider to win the Tour four times.

At the World Championship road race in Ronse, Anquetil was leading alone with 0.6 mile ^{(1 km)} ahead of the chasing field, but eased his effort when he turned around to see the other riders approaching. After the finish, second-placed van Looy was irritated at Anquetil, stating that he had given up his chance at certain victory. Towards the end of the season, he competed in the Trofeo Baracchi, partnered with Poulidor, where they finished second. For the second time, he won the Super Prestige Pernod for the best rider of the season.

2.5.5. 1964: Giro d'Italia, a Fifth Tour de France, and the Duel with Poulidor

At the beginning of the 1964 season, Anquetil raced at Paris-Nice again, being beaten in the uphill time trial by Poulidor and finishing only sixth. When he lined up for the spring classic Gent-Wevelgem, few expected much of him, since Anquetil did not usually excel at one-day races. A few kilometers before the finish, Anquetil, unfamiliar with the course, asked another rider where the finish was. Given the answer that it was not far away, he broke away from the field for an unlikely victory, his first at a one-day road race outside of France. For 1964, Anquetil had again set himself the target to emulate Coppi by winning the Giro and the Tour in the same year. He started the Giro d'Italia strongly, winning the stage 5 time trial at a speed of over 30 mph ^{(48 km/h)}, taking the race lead in the process. Though he was unable to add another stage victory, he would not lose the pink jersey until the finish in Milan, beating Italo Zilioli by 1:22 minutes.

The 1964 Tour de France would become a two-man fight between Anquetil and Poulidor. The latter lost 14 seconds after a crash on the first stage, but took some time back when he escaped in a group on stage 7, with Anquetil reaching the finish 34 seconds behind. The next day, Anquetil lost another 47 seconds, as Poulidor finished second and Anquetil suffered a puncture. On stage 9, finishing in Monaco, Poulidor sprinted for the stage victory and celebrated, only to realize there was another lap to run. The second time around, it was Anquetil who won the stage and with it a one-minute time bonus. The next day, Anquetil also won the time trial, taking another 46 seconds advantage on Poulidor. In the general classification, Anquetil now was second, with Poulidor third, 31 seconds behind. During the rest day in Andorra, Anquetil, known for his extravagant eating habits, was pictured eating a méchoui, an entire lamb. The next day, stage 14, Anquetil started badly, falling behind on the first climb and even contemplating retiring from the race. Being four minutes behind Poulidor, Bahamontes, and yellow jersey Georges Groussard, Anquetil found himself in a group of seven riders who worked well together and succeeded in bridging the gap. Poulidor then had to change bikes with 17 mile ^{(28 km)} to go, and fell into the ditch when his director pushed him too hard when he got going again. By the end of the stage, Poulidor had lost 2:37 minutes on Anquetil. Poulidor managed to record a strong solo victory on the following stage into Luchon, gaining enough time to close the gap on Anquetil in the general classification to just nine seconds. In the stage 17 time trial, Anquetil took victory, but Poulidor managed to reduce his losses to just 37 seconds, even though he suffered a puncture and a slow bike change, leaving him 56 seconds down on Anquetil overall. Stage 20 was the decisive leg of the race, ending on the Puy de Dôme climb. Poulidor attacked early in the stage, but was brought back by Anquetil with the help of Altig. As they reached the final climb, Bahamontes and Julio Jiménez escaped, while Anquetil and Poulidor made the ascent side-by-side. In what would become one of the Tour's most historic stages, the two opponents went up the climb elbow to elbow, until 2953 ft ^{(900 m)}, Anquetil weakened, allowing Poulidor to slowly get ahead of him. By the finish, Poulidor had taken 42 seconds out of Anquetil's advantage, who remained in the yellow jersey. After crossing the finish line, Anquetil asked Géminiani how much time he had lost. When his sporting director answered "Fourteen seconds", Anquetil replied: "Well, that's thirteen more than I need." Anquetil then went on to win the final time trial into Paris, extending his eventual winning margin to 55 seconds over Poulidor. It was Anquetil's fifth Tour victory, and the fierce duel between him and Poulidor started a cycling boom in France. Anquetil became the first rider since Coppi to win both the Giro and the Tour in the same year.

Anquetil raced little after the Tour, finishing seventh at the World Championships in Sallanches and skipping all of the end-of-season time trials.

2.6.1. 1965: Critérium du Dauphiné Libéré and Bordeaux-Paris

For 1965, Saint-Raphaël ceased sponsoring Anquetil's team, which was then taken over by Ford France. In those days, the primary income for professional cyclists came from criteriums, small races held over laps in city centers, usually shortly after the Tour de France. Anquetil had realized that winning more Tours would not significantly increase his value in terms of start money, so he chose not to race any of the three Grand Tours in 1965. Early in the season, he won both Paris-Nice and the Critérium National and also participated for three days in the Monte Carlo Rally to appease his new sponsor, Ford.

Instead of the Grand Tours, Géminiani proposed another feat: the 1965 Critérium du Dauphiné Libéré ended on the same day that the 348 mile ^{(560 km)} classic Bordeaux-Paris began, a race partly conducted behind dernys due to its excessive length. Géminiani pitched the idea to Anquetil's wife, Jeanine, who then convinced her husband to attempt to win both races. The announcement of this audacious attempt made headlines, bringing significant publicity to both events. The organizers of the Critérium du Dauphiné, initially reluctant, eventually aided the attempt by moving the start time of the final stage one hour forward to give Anquetil enough time to travel from Avignon (the Dauphiné's finishing town) to Bordeaux. At the Critérium du Dauphiné, Anquetil won narrowly, primarily through time bonuses at stage finishes and a slender victory in the time trial. He ultimately won the race by 1:43 minutes over Poulidor. Just 15 minutes after standing on the podium at 5 pm, Anquetil was in a car, being driven to a hotel for a bath and dinner, before heading to Nîmes airport to board a private jet that flew him to Bordeaux. The race to Paris started in the middle of the night, and Anquetil, having not slept, suffered at the beginning. Coming close to retiring in the early hours of the morning, he was convinced by his teammates to continue. He eventually joined a breakaway with Tom Simpson and Stablinski, then attacked on the Côte de Picardie climb, 5.0 mile ^{(8 km)} from the finish, and went on to win the race by 57 seconds ahead of Stablinski.

After failing to finish the World Championships in San Sebastián, Anquetil returned to the end-of-season time trials. He won the Grand Prix des Nations ahead of Altig and then beat Gianni Motta at the Gran Premio di Lugano. Anquetil then won his second Trofeo Baracchi, partnered with Stablinski. For the third time, Anquetil won the Super Prestige Pernod.

2.6.2. 1966: Grand Tour Return and Liège-Bastogne-Liège Victory

Anquetil started 1966 strongly with a victory at the Giro di Sardegna. At Paris-Nice, he was in the race lead but lost time to Poulidor on a hilly time trial because his bike was not fitted properly. Anquetil then formed an alliance with the Italian riders, including Gianni Motta, and their joint attacks pressured Poulidor, allowing Anquetil to win the stage and the overall race. In early May, he was on the start line for Liège-Bastogne-Liège, the oldest race on the cycling calendar and one of the sport's so-called monuments. Anquetil felt he had a chance of victory and escaped alone from a group containing Motta, Felice Gimondi, and a young Eddy Merckx. Although the trio worked well together to chase him, Anquetil's advantage continued to grow until the finish, where he won by almost five minutes. After the finish, while conducting interviews, he was approached and told he needed to provide a urine sample for doping control, but he ignored it and left. The next day, news broke that he had been disqualified by the Belgian cycling federation for his refusal. Following Anquetil's insistence that he had not been officially approached for the test, the authorities relented, and his victory was allowed to stand.

Unlike the previous year, Anquetil lined up for the 1966 Giro d'Italia. On the very first stage, he suffered two flat tires when an overenthusiastic fan tried to give him water, fell, and the glass bottle broke on the ground. A 22-rider group, containing all the other favorites, got away while Anquetil's tires were being attended to, and at the finish, he had lost 3:15 minutes. A second-place finish behind Vittorio Adorni in the stage 13 time trial brought him up to tenth place overall, but Anquetil no longer felt he could win the Giro and focused on preventing Gimondi from winning, as he considered the rising popularity of the young Italian a threat to his financial opportunities during the criteriums. After some strong riding in the mountain stages, Anquetil eventually finished third in the Giro, 4:40 minutes behind winner Motta.

The 1966 Tour de France was again expected to be a battle between Anquetil and Poulidor. On stage 9, Anquetil led a strike by the riders against the newly established anti-doping controls. Both Anquetil and Poulidor mainly marked each other, allowing Anquetil's teammate Lucien Aimar and Jan Janssen to gain time on stage 10. Poulidor won the time trial on stage 14b, seven seconds ahead of Anquetil. On stage 17, Aimar took advantage of the stalemate to break away from the lead group, win the stage, and take over the race lead. Anquetil, weakened by illness, helped Aimar by chasing down attacks from Janssen and Poulidor over the next stage before dropping out the following day. Aimar eventually won the Tour ahead of Janssen and Poulidor.

After the Tour, Anquetil competed at the World Championships held on the Nürburgring racing circuit. Late in the race, Anquetil and Poulidor were in a leading group with Motta, but both Frenchmen did not work together, allowing Altig to catch back up. In the final sprint to the line, Altig, by far the best sprinter, easily won, taking the title on home soil. Anquetil finished second, ahead of Poulidor, the highest position he would ever achieve in the World Championships. Anquetil then started and won the Grand Prix des Nations for the ninth time in his career, the final time he would ride the race. In the Super Prestige Pernod, Anquetil was highly placed going into the final race of the competition, the Giro di Lombardia. He finished fourth, earning him enough points to win the season-long competition for the fourth and last time in his career.

2.6.3. 1967-1969: Final Years and Invalidated Hour Record Attempt

With Ford France pulling out of sponsorship, Anquetil, like many of his teammates and director Géminiani, switched over to the Bic team. By 1967, Anquetil started to appear in fewer one-day races but lined up on short notice at the Critérium National, held in his hometown of Rouen, and won. Anquetil then again started at the Giro d'Italia, losing some time early on, before moving into the pink jersey with a fourth place in the stage 16 time trial, as all other favorites put in poor rides. He lost the lead the next day to Silvano Schiavon, who had shared a successful breakaway with Franco Balmamion. Having lost all but two teammates by the start of stage 20, Anquetil managed to limit his losses on the stage to regain the overall lead, albeit just 34 seconds ahead of Gimondi. During the following stage, he fended off several attacks, but eventually Gimondi managed to escape, gaining 4:09 minutes on Anquetil, relegating him to second place. On the penultimate stage on the final day, Anquetil made several attacks but was unable to break away from Gimondi. Thus tired, he proceeded to lose second place to Balmamion and finished the Giro in third. In 2012, it was revealed that former deputy race director Giovanni Michelotti admitted late in his life to having aided Gimondi on stage 21 by giving him the slipstream of the race organization's car as he was riding away from Anquetil. He allegedly did so to make up for the fact that he had annulled the result of stage 19 to Tre Cime di Lavaredo after many riders had been pushed up the climb by spectators. Gimondi had originally won that stage and gained the pink jersey before the result was taken back.

For its 1967 edition, the Tour de France reverted to national teams, and Marcel Bidot picked Poulidor as leader, while Anquetil stayed away. He instead decided that he would make an attempt at breaking Rivière's now eleven-year-old hour record. On 27 September, he made the attempt, again at the Velodromo Vigorelli, beating the record by 479 ft ^{(146 m)}. After Anquetil finished his ride, he was approached by the doctor appointed by the sport's governing body, the Union Cycliste Internationale (UCI), to conduct his doping test. Géminiani protested that there was no lavatory on site at the velodrome and that Anquetil would not provide the urine sample out in the open. Since the doctor refused to travel with Anquetil to his hotel, no test was done, and Anquetil's record was therefore never ratified by the UCI. For the first time in his career, Anquetil was not chosen as part of the French team at the World Championships, but Anquetil managed a second place at the Trofeo Baracchi, partnering Bernard Guyot, to end his season. At the end of the year, Anquetil became chairman of the French Professional Cyclists Union, responsible for advocating the riders' interests towards the governing bodies and race organizers.

The final two seasons of Anquetil's career were relatively quiet. He did not race much in 1968, with his only victory coming at the Trofeo Baracchi, riding together with Gimondi. In 1969, he finished third at Paris-Nice and then won the Tour of the Basque Country, his last victory as a professional. His last professional race on the road was the World Championship road race in Zolder, where he placed 40th. He participated in a number of autumn criteriums and raced for the last time in Paris at the La Cipale velodrome at a track event; the venue would later be named after him. Anquetil's final outing was at a track event in Belgium on 27 December 1969.