The Most Successful Vuelta a España Cyclists

The 2024 edition is now underway and, as ever, we can expect three weeks of intense cycling action, as well as stunning views of the Spanish countryside and Pyrenees region. Sportsbooks will be working overtime on their La Vuelta cycling betting markets as the stages of the Grand Tour are played out.

As we wait to see who becomes the latest name to go down in the tour’s history books and emulate Sepp Kuss’ victory of last year, we thought we would take a nostalgic look back at the riders who have won the Vuelta a España the most times down through the years.

There are a whole host of famous names that can claim multiple wins at La Vuelta, with many top cyclists boasting two titles. But if we were to pull one name out of the pack to highlight in that class, it should really have to be this Belgian road racing legend. Not only did he win the very first Vuelta a España, he followed it up with another title the very next year.

Who knows how successful Deloor might have been? His cycling career began in 1932 but was cruelly cut short by the outbreak of war in 1939. Deloor did survive WW2 but moved to the US after hostilities ended and never raced competitively again. After winning the first event in 1935, the Deloors made the next year a family affair, with Gustaaf finishing just ahead of his brother Alfons. Gustaaf also managed to win a stage in the Tour de France in 1937.

Many multiple winners of La Vuelta have come in more recent years and our next legendary cyclist is an athlete who has become one of the greatest ever in the sport. The Slovenian cyclist actually started off his professional life as a ski jumper but switched to two wheels after a particularly nasty injury.

Moving to cycling was the best thing that Roglić could ever have done. After only five years in the sport, he became the first-ever Slovenian to win a stage at the Tour de France. He had already won a stage at the Giro d’Italia a year previously – but greater success was to come. In 2019 Roglić won his first Grand Tour – the Vuelta a España – and proceeded to dominate the event, claiming the title again in 2020 and 2021.

Although Roglić has raced somewhat in the shadow of compatriot Tadej Pogačar in recent years, he has also finished on the podium of all three Grand Tours and managed to win the Giro d’Italia last year. A crash ended his Tour de France this season but there are surely more triumphs ahead for Roglić.

There might not have been as many Spanish winners of La Vuelta as you might imagine, but one of the names that has definitely gone down as one of the event’s greats is Alberto Contador. A multiple winner, Contador claimed his titles across a much longer time period than some of his contemporaries, winning his first in 2008 and claiming a third in 2014.

Now retired, Contador didn’t save his best for his home nation Grand Tour either. At his peak, he was one of the best in the business, also claiming two Tour de France titles and two in the Giro d’Italia. His haul puts him in exalted company as one of just six riders to win all three Tours – and one of just two to win all three multiple times.

Unsurprisingly, Contador was regarded as a master of the mountains and was an excellent climber. His time trial stages could also be event-leading and he even came back from a suspension to win events and tours. A champion to the end, Contador won a mountain stage of La Vuelta on the penultimate day of his career before retiring.

Although, like many cyclists, his career has been sometimes mired in controversy over drug-taking, Tony Rominger is a name that is well known by Vuelta a España fans, with the Swiss rider claiming the general classification win on three occasions. In fact, like other multiple champions, Rominger won back-to-back titles, dominating the event from 1992 to 1994.

Another latecomer to the sport, Rominger packed a lot into his cycling career, winning his first Grand Tour stage at the 1988 Giro d’Italia. He actually won the general classification in that event in 1996, although his most prestigious achievement at the Tour de France was the mountains classification in 1993.

Rominger obviously felt more at home at the Vuelta a España though, with those three La Vuelta titles being a record at the time.

As a rider who raced alongside Lance Armstrong, Roberto Heras’ career has long been a topic of conversation. The Spanish cyclist has faced lengthy legal battles to prove his innocence after having titles stripped because of alleged positive tests. But now Heras can be heralded as the most successful cyclist in the history of the Vuelta a España.

Turning professional in 1995, Heras had limited success in the other two Grand Tours but dominated La Vuelta for a time at the beginning of the millennium. Between 1997 and 2005, Heras finished in the top five every year except one, when he finished in sixth position. Glory first came in 2000, with further titles won in 2003, 2004, and 2005.

Heras was initially disqualified in 2005, leaving Roglić, Contador, and Rominger as the most winningest cyclists in the event. But in 2011 he was finally cleared, the 2005 title was handed back, and Roberto Heras could once again be named as the most successful rider in the history of the Vuelta a España.