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Rik Van Looy
Born
The first rider to win all five monuments, Van Looy won Paris-Roubaix three times and Flanders twice in the 1950s and 1960s. He was a sprinter strong enough to survive the cobbles, and his "red guard" of team-mates riding the front for him set the template for how teams still control a classic.
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Eddy Merckx
Born
Merckx won 19 monuments, including seven Milan-San Remos and five Liège-Bastogne-Lièges, alongside three Roubaix and two Flanders titles. No one else has won so often on such different terrain, from the flat run-in to San Remo to the long Ardennes climbs, and the sheer range is the point: he could attack anywhere.
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Roger De Vlaeminck
Born
"Monsieur Paris-Roubaix" won the race four times in the 1970s and also won all five monuments. A former cyclo-cross world champion, he rode the pavé with a lightness that kept him upright when others crashed, and his career is the best evidence that bike handling matters as much as power on the cobbles.
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Sean Kelly (cyclist)
Born
The Irishman won nine monuments in the 1980s and early 1990s: two Milan-San Remos, two Roubaix, two Liège and three Lombardias, missing only Flanders, where he was second three times. Kelly thrived in cold, wet races that broke others, and his descent of the Poggio to win San Remo in 1992 is still studied.
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Moreno Argentin
Born
Argentin won Liège-Bastogne-Liège four times and Flèche Wallonne three times, the purest Ardennes record of the late 1980s and early 1990s, and added the 1990 Tour of Flanders. He shows how a punchy climber with a sprint could win on both the short Ardennes walls and the cobbled bergs.
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Johan Museeuw
Born
"The Lion of Flanders" won the Tour of Flanders and Paris-Roubaix three times each in the 1990s and early 2000s. His 2002 Roubaix, won alone in mud after recovering from a gangrene scare caused by a crash in the Arenberg Forest, shows the specific toll the cobbles take. He later admitted to doping during his career.
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Erik Zabel
Born
Zabel won Milan-San Remo four times between 1997 and 2001, the specialist sprinter's answer to the classics. His wins show what San Remo really is: 290 km of patience, then holding the wheel over the Cipressa and Poggio for a flat finish on the Via Roma. He also later admitted to doping in that period.
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Paolo Bettini
Born
"Il Grillo", the cricket, won Liège twice, Milan-San Remo in 2003 and Lombardia twice, plus Olympic and world road titles. Small and explosive, he won by jumping clear on short climbs and holding on, which made him the model one-day rider for hilly courses in the 2000s.
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Tom Boonen
Born
Boonen won Paris-Roubaix four times and Flanders three times between 2005 and 2012, equalling the cobbled records. A big rider who could sprint, he won either by surviving the cobbles with the leaders or, in his 2012 Roubaix, by riding away alone with over 50 km left. The clearest modern case for Roubaix suiting heavier riders.
More about Tom Boonen10
Fabian Cancellara
Born
Cancellara won Flanders and Roubaix three times each plus Milan-San Remo in 2008, using the steady power of a time-trial world champion. His style was the long solo: open a gap on a cobbled sector and ride the rest as a time trial, a tactic that only works when the legs and the terrain align.
More about Fabian Cancellara11
Philippe Gilbert
Born
Gilbert won four of the five monuments, Lombardia twice, Liège, Flanders and Roubaix, and in 2011 took Amstel, Flèche and Liège in one week. He started as an Ardennes puncheur and reinvented himself for the cobbles in his thirties, which makes his career the best illustration of how differently those races ask to be ridden.
More about Philippe Gilbert12
Alejandro Valverde
Born
Valverde won Liège-Bastogne-Liège four times and Flèche Wallonne five times, mastering the Mur de Huy's steep final kilometre like nobody else. His Ardennes record over 15 years, interrupted by a doping ban, shows what timing a single effort on one specific climb can do.
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Peter Sagan
Sagan won Flanders in 2016 and Roubaix in 2018, along with three straight world titles and Gent-Wevelgem three times. His bike handling on wet, narrow Flemish roads was exceptional, and he regularly attacked from distance rather than waiting for the sprint his speed would have allowed.
More about Peter Sagan14
Mathieu van der Poel
Born
Van der Poel has won Flanders three times, Paris-Roubaix three times in a row from 2023 to 2025 and Milan-San Remo twice. The cyclo-cross world champion brings off-road handling and repeated explosive efforts to the cobbles, and his Roubaix wins came from attacks on sectors where others were just trying to stay upright.
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Wout van Aert
Born
Van Aert won Milan-San Remo in 2020 and, after years of near misses and bad luck, Paris-Roubaix in 2026, outsprinting Pogačar in the velodrome. Another cyclo-cross convert, he combines time-trial power with a sprint, and his long wait for a cobbled monument shows how much luck with punctures and crashes these races demand.
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Tadej Pogačar
Born
A Grand Tour climber who also wins classics: Pogačar has won Flanders three times, Liège four times, Milan-San Remo in 2026 and Lombardia five years running, with Roubaix the only monument missing after two second places. He wins Flanders by attacking on the Oude Kwaremont until no one can follow, a tactic only possible with climbing power on short bergs.
More about Tadej Pogačar17
Remco Evenepoel
Born
Evenepoel won Liège-Bastogne-Liège in 2022 and 2023, both times by riding clear on the climbs and holding off the group as a time triallist would, and added the Amstel Gold Race in 2026. He is the current best example of an Ardennes winner who wins by sustained power rather than a final kick.
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Marianne Vos
Born
Vos won Flèche Wallonne five times, the 2013 Tour of Flanders and a long run of other one-day races across two decades, while also winning cyclo-cross and Olympic titles. Her sprint after a hard race made her a threat on almost any classic terrain, and she was still winning big races into her late thirties.
More about Marianne Vos19
Anna van der Breggen
Born
Van der Breggen won Flèche Wallonne seven years in a row (2015 to 2021), plus two Liège titles and the 2018 Tour of Flanders. Her Mur de Huy record is the women's equivalent of Valverde's: a climber's acceleration timed on the same steep ramp year after year.
More about Anna van der Breggen20
Lizzie Deignan
Born
The Yorkshire rider won the Tour of Flanders in 2016, Liège in 2020 and the first Paris-Roubaix Femmes in 2021, attacking alone on the first cobbled sectors in the wet and staying away. Few riders have won on Flemish bergs, Ardennes climbs and flat pavé, which is exactly why she belongs here.
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Elisa Longo Borghini
Born
Longo Borghini won Flanders in 2015 and 2024 and Paris-Roubaix in 2022, nine years apart on the bergs. A strong climber with patience, she tends to win from small groups after a hard race rather than with a single attack, which suits Flanders' accumulating fatigue.
More about Elisa Longo Borghini22
Lotte Kopecky
Born
Kopecky won Flanders in 2022 and 2023, Paris-Roubaix in 2024 and Milan-San Remo in 2026. A track rider with a fast finish who also climbs the short bergs well, she can win from a sprint or a small group, which makes her the most complete cobbled-classics rider in the current women's peloton.
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Demi Vollering
Born
Vollering swept Amstel, Flèche and Liège in 2023, won Liège again in 2026 for a third title, and took the 2026 Tour of Flanders. A climber first, she is the clearest case of an Ardennes specialist extending her range to the cobbles.
More about Demi Vollering24
Pauline Ferrand-Prévot
Born
A former world champion on the road, in cyclo-cross and in mountain biking, Ferrand-Prévot returned to road racing and won Paris-Roubaix Femmes in 2025 with a solo attack. Her off-road skills are visible on the pavé, and her switch between disciplines is unusual even in an era of cross-over riders.
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