Greatest Upsets from the Tour de France

In 2005, cycling team Shimano-Memory Corp were the greenest squad hoping to reach the WorldTour level. The going was slow, but by 2009, the team’s fanatical efforts landed them a wildcard at the 2009 Tour de France.

In 2011, the team lost a major sponsor. A last-minute investment from an oil group in the Netherlands kept the team afloat. They changed from Shimano-Memory Corp to Argos-Shimano, then continued on to qualify for the 2012 Tour de France.

By 2013, the team were competing at WorldTour level. A car accident in 2016 prior to the 2016 Tour de France caused further setbacks, but ultimately led to a meteoric rise in 2017. Rebranded as team Sunweb, the squad took the 2017 Giro d’Italia, then won four stages and two major jerseys at the 2017 Tour de France.

Watching an underdog come-up story like Team Sunweb’s 2012 to 2017 saga is something sports fans relish about cheering on their favorite athletes. When it comes to wagering on cycling, knowing which underdogs to back can be difficult given the range of competition and shifting rosters.

For those looking to find a reliable sportsbook that offers quality insight into cycling, this guide will help you sift through the ample offerings out there. After all, wagering on the Tour de France or another Grand Tour isn’t just about knowing the teams, but also understanding industry dynamics and stats for individual cyclists.

Even so, the Grand Tours are subject to external circumstances that can’t be predicted. This includes factors such as weather, as well as heart. The WorldTour may not see upsets often, but the underdogs who come out on top won’t be forgotten any time soon.

Greg LeMond Overtakes Laurent Fignon

The 1989 Tour de France came down to eight seconds and two aggressive competitors: French favorite Laurent Fignon and American Greg LeMond. To this day, LeMond’s eight-second overtake of Fignon is known as the greatest upset in the Tour’s history.

Not only is the race the closest on Tour de France record, but it highlighted the grueling nature of the sport. Fignon rode 3,825km, fighting across 21 stages, only to be usurped by a matter of seconds.

Twenty years after the fateful day, LeMond released an autobiography. The first chapter is titled ‘Eight Seconds’. 

Primož Roglič Takes Stage 17

The 2017 WorldTour season wasn’t short on underdog heroes. Following a slew of crashes involving the biggest names from teams like Movistar and Dimension Data, cycling fans knew they were in for a treat.

The only American team managed to take stage 9, while one Dutch squad, LottoNL-Jumbo, ended a three-year losing streak with a win at stage 17. To do that, LottoNL-Jumbo cyclist Primož Roglič had to defy the odds.

Not only was Roglič fighting with less sponsorship power than other competitors, but it was also his debut Tour appearance. Add to that the fact that Roglič became the first Slovenian to win a Tour stage and it’s easy to see why his efforts will be remembered for years to come.

Jacky Durand Takes Three Tour Wins

Those who remember Jacky Durand know the cyclist as a scrappy, aggressive racer—a perfect underdog prototype. His long solo attacks riled the spirits of spectators though they were rarely successful, while his personality stoked strong reactions.

Durand’s greatest upset wasn’t the Tour de France, but his 1992 nab of the Tour of Flanders. However, his ability to overtake leading competitors also helped him take three wins at the French Grand Tour; stage 10 in 1994, the prologue in 1995, and stage 8 in 1998 (along with a combativity award).

One of his most famous quotes is, “It astonishes me that most riders are followers, even sheep.”


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