Philippe Gilbert this week outlined his ambitions of winning all five monuments during his career. He has previously taken victory in both Liege-Bastogne-Liege and the Tour of Lombardy, and now wants to try and win the remaining three. He stated “My dream is to win every classic at least once. I just have Milan-San Remo, Tour of Flanders and Paris-Roubaix (remaining).

Next year, he intends to take part in Flanders and Roubaix rather than the Ardennes. So, how difficult would it be for him to win all five? The quick answer is “very difficult”.

Only three cyclists have won all five to-date, namely the three Belgians Eddy Merckx, Roger de Vlaeminck and Rik van Looy. Five others managed to win four, Germain Derycke, Fred de Bruyne, Louison Bobet, Hennie Kuiper and Sean Kelly. So, it’s a big ask for Gilbert.

The table below shows those with the most monument wins.

Classics Winners


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