With his victory at Liege-Bastogne-Liege in 1961, Belgian legend Rik Van Looy, the “Emperor” became the first cyclist ever to win all the five Monuments.
He won Milano-Sanremo in 1958, Ronde van Vlaanderen in 1959 and 1962, Giro di Lombardia in 1959, Paris-Roubaix in 1961,1962, and 1965.
Nevertheless, the race on 15 May 1961, when he won Liege-Bastogne-Liege, wasn’t that eventfull like the day when Roger De Vlaemick managed to win his fifth Monument.
Besides them, the third cyclist who managed to win all the five historic one-day races is, of course, Eddy Merckx.
During his successfull career, Philippe Gilbert won four of them (Giro di Lombardia 2009, 2010, Liege-Bastogne-Liege 2011, Ronde van Vlaanderen 2017, Paris-Roubaix 2019) missed only a Milano-Sanremo victory.
Currently Mathieu van der Poel (Ronde van Vlaanderen 2020, 2022, 2024 Milano-Sanremo 2023, Paris-Roubaix 2023, 2024) and Tadej Pogacar (ll Lombardia 2021, 2022, 2023, Liege-Bastogne-Liege 2021, 2024, and Ronde van Vlaanderen 2023) are the closest to win all the five Monuments for at least once during their career. Also, they both won Strade Bianche, which is quite often called “the 6th Monuments” nowadays. Why this seems to be unfair from a historical point of view? -I wrote about it here.