The degree of difficulty also shifted
over the decades. The Tour in the 1950s and 60s was longer, with vast gaps between stages, whereas modern Grand Tours feature scientific preparation, highly specialised teams and far deeper international depth. In every case, though, the challenge was the same: endure three weeks of mountains, time trials, fatigue and pressure.
These are the years in which each rider first won each of the three Grand Tours and, crucially, how those victories built one of the most exclusive clubs in sporting history.
Jacques Anquetil
Anquetil broke trail in 1957, winning his first Tour de France at just 23. It was a commanding triumph that announced a time trial specialist set to dominate the decade. He faced climbers like Federico Bahamontes and riders of Marcel Janssens’ calibre. The Frenchman leaned on his formidable ability against the clock to offset losses in the mountains and ultimately imposed an authority few expected from someone so young.
Three years later came the 1960 Giro. Italy proved far trickier, with Gastone Nencini as the main rival and a battle that forced Anquetil to meter his efforts carefully. He prevailed in an edition shaped by the mountains and by the need to resist attacks from Italian specialists. That win confirmed his dominance wasn’t confined to the Tour and brought him closer to the select target of all three Grand Tours.
The 1963 Vuelta completed the circle. Anquetil became the first rider to conquer all three, doing so in a particularly demanding Vuelta for the era. The Spanish victory also had a strategic edge: once again he relied on consistency and time trial strength to keep his main rivals in check. The result turned a collection of major wins into a lasting legacy.
Felice Gimondi
Gimondi began his trilogy at the 1965 Tour, on debut. The Italian stunned the field, beating illustrious rivals and showing a rare blend of climbing and time trialling. The race was defined by the severity of the Alps and Pyrenees, but Gimondi maintained the steadiness needed to outlast Raymond Poulidor and other specialists of the time.
In 1967 he seized the Giro d’Italia, his first Grand Tour at home. It was a far more open contest, with rivals like Jacques Anquetil and Italian riders intimately familiar with the terrain. Gimondi faced a long, mountainous route where endurance mattered as much as punch. The victory confirmed that the 1965 Tour winner could also command the Corsa Rosa.
La Vuelta arrived in 1968 and with it Gimondi’s entry into the club Anquetil had founded. The Italian mastered a demanding route and an international field packed with quality. His win in Spain carried huge symbolic weight: it proved he could adapt to varied terrain and remain relentlessly consistent over three weeks.
Eddy Merckx in action in 1974.
Eddy Merckx
Merckx opened his Grand Tour collection at the 1968 Giro d’Italia. He had yet to win the Tour but was already an extraordinary force. In Italy he faced Felice Gimondi and the era’s best, imposing a blend of power, endurance and aggression that heralded the dominance to come.
A year later came the 1969 Tour de France. It was Merckx’s definitive unveiling as cycling’s supreme ruler. The Belgian did far more than control the standings: he won mountain stages, time trials and built vast gaps on rivals such as Felice Gimondi and Roger Pingeon. The brutality of that edition was reflected in the scale of his victory.
The 1973 Vuelta completed his personal trilogy. Merckx had to face Luis Ocaña and José Manuel Fuente, two exceptional climbers, in a race shaped by Spain’s mountains.
The win was especially significant because it came after years of dominance at the Giro and the Tour. With it, Merckx joined the select group of riders who held all three Grand Tours on their palmarès at the same time.
Bernard Hinault
Hinault captured La Vuelta in 1978, in the first great season of his dominance. The Frenchman faced Joop Zoetemelk, Joaquim Agostinho and other specialists in a demanding race that he won with authority. It was the opening act of an extraordinary campaign, with the Tour looming just weeks later.
At the 1978 Tour, Hinault confirmed his arrival among the greats. Zoetemelk was his main rival and even wore yellow, but Hinault settled the race in the final time trial. The edition was notably hard and further marked by the expulsion of Michel Pollentier, who had led the standings before being sanctioned for attempting to cheat the anti-doping control.
Two years later, Hinault won his first Giro. The 1980 Corsa Rosa pitted him against Wladimiro Panizza, Giovanni Battaglin and Giuseppe Saronni. The Frenchman had to navigate a mountainous and tactical race, but ultimately imposed his superiority to claim the maglia rosa by more than five minutes over Panizza.
Alberto Contador on the ascent to the Colle delle Finestre at the Giro d’Italia
Alberto Contador
Contador opened his path at the 2007 Tour de France. At just 24, the Spaniard prevailed in a race defined by parity and the constant pressure of riders like Cadel Evans and Levi Leipheimer. The mountains proved decisive and Contador used his punch to become the youngest winner of that edition.
In 2008 he conquered the Giro d’Italia, a particularly complex victory as he was drafted in late and had to face Riccardo Riccò and Danilo Di Luca. The battle stayed open until the final time trial in Milan, where Contador defended his narrow lead. He became the first Spaniard to win the Giro since Miguel Indurain.
Months later he completed the trilogy at La Vuelta. The 2008 edition featured Levi Leipheimer, Carlos Sastre and Alejandro Valverde as chief rivals. Contador seized the lead after the Angliru and consolidated it in the mountains and the time trial. At just 25 he became the first Spaniard to conquer all three Grand Tours.
Vincenzo Nibali
Nibali began his collection with the 2010 Vuelta. The Italian had to overcome Joaquim Rodríguez and Ezequiel Mosquera in a race of severe climbing. The fight stayed alive to the end and Nibali showed outstanding composure both on the ascents and through the transition stages.
His first Giro arrived in 2013. The edition was marked by bad weather and mountains, with Rigoberto Urán and Cadel Evans as main rivals. Nibali had been third in 2010 and second in 2011 before returning to finally claim the maglia rosa. Urán finished second and Evans third, underlining the quality of the podium.
In 2014 came his masterpiece: the Tour de France. With Chris Froome and Alberto Contador out of the final fight, Nibali faced Jean-Christophe Péraud, Thibaut Pinot and Alejandro Valverde. The Italian controlled the race from the opening week and won by a wide margin. It was his most emphatic triumph and the one that completed his set.
Chris Froome
Chris Froome in action at La Vuelta a España 2017
Froome’s first major title was the 2011 Vuelta, although the race was initially awarded to Juan José Cobo. After the Spaniard’s later sanction, Froome was recognized as the winner. That Vuelta was extremely tight and the Briton finished just 13 seconds behind Cobo in the original standings, after also duelling with Bradley Wiggins and Bauke Mollema.
The 2013 Tour was his breakthrough. Froome arrived as Wiggins’s heir and had to measure himself against Nairo Quintana, Joaquim Rodríguez and Alberto Contador. The French mountains and the time trials allowed him to build a solid advantage and win his first Tour, launching the Sky era of dominance.
Five years later, Froome completed the trilogy at the 2018 Giro. It was one of the peloton’s most spectacular victories: Simon Yates dominated much of the race, but Froome overturned the general classification with his long-range attack on the Colle delle Finestre. He finally beat Tom Dumoulin and Miguel Ángel López. He also became the first Briton to win the Corsa Rosa.
Jonas Vingegaard
Vingegaard began his path at the 2022 Tour de France, defeating Tadej Pogačar for the first time in a battle that reshaped modern cycling. The race was marked by heat, echelons, cobbles and, above all, an intense fight in the mountains. The Dane imposed himself on the Slovenian thanks to growing superiority in the Alps and the Pyrenees.
In 2025 came La Vuelta. Vingegaard faced João Almeida and Tom Pidcock in an especially demanding edition, with finishes like the Angliru and the Bola del Mundo. The Dane won by 1:16 over Almeida and 3:11 over Pidcock. His victory was also framed by protests that interrupted the final stage in Madrid.
The last step arrived at the 2026 Giro. On his Corsa Rosa debut, Vingegaard won five of the six summit finishes and ended 5:22 ahead of Felix Gall and 6:25 ahead of Jai Hindley. The 3,466-kilometre race with over 49,000 metres of climbing confirmed the scale of the challenge. In Rome, the Dane completed the trilogy and became the eighth man in history to win all three Grand Tours.
Eight names, eight eras and eight different routes. Anquetil opened the door in 1963; Gimondi, Merckx, Hinault, Contador, Nibali and Froome kept it a guarded preserve for decades. Now Vingegaard has added his name to a list that seems ever harder to expand. In a sport where winning a single Grand Tour already demands an exceptional blend of talent, team, endurance and luck, conquering all three remains one of the greatest tests of greatness.