Pogacar is racing toward something never before seen in cycling

Achieving victory in the five Monuments of cycling, namely, Milan-San Remo, Tour of Flanders, Paris-Roubaix, Liege-Bastogne-Liege, and Il Lombardia is one of the great challenges of cycling. In fact, only 3 cyclists throughout history can boast of such a feat, while, in comparison, there are 7 cyclists who have managed to win the three Grand Tours. Now, Mathieu van der Poel could join this exclusive list.

Which cyclists have won the 5 Monuments of Cycling

In the world of cycling, there are several exclusive lists, clubs of select winners, those who have achieved certain challenges that very few others have managed to conquer. We have, for example, those who have won the Tour de France 5 times, including those who are considered by many to be the greatest cyclists in history. We also have those who have managed to win at least once in the Giro, Tour, and Vuelta, known as the triple crown.

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However, the most exclusive of all is the one that groups together the winners of the five monuments, the most iconic classics of cycling, a list composed of only 3 names that has not increased since the 1970s, demonstrating the magnitude of achieving such a feat. In fact, in recent years, only Philippe Gilbert has been in a position to have achieved the full set of monuments, although he fell short in the Milan-San Remo, which is said to be the most difficult classic to win.

This list is composed curiously of three Belgian cyclists: Rick Van Looy, Roger de Vlameminck and, unsurprisingly, one who is present in all cycling statistics we consider, the omnipresent Eddy Merckx.

The latter hardly needs an introduction, as he was known as the Cannibal. A cyclist who practically raced in every event and in every race not only aimed to win, but to dominate his rivals. It didn't matter if it was a stage race, a one-week race, a classic, or a kermesse in any village in Belgium.

Eddy Merckx also holds the record for the most monuments in his extensive list of achievements, with no less than 19 victories spread among his 7 Milan-San Remo, 2 Tour of Flanders, 3 Paris-Roubaix, 5 Liege-Bastogne-Liege, and 2 victories in Lombardia.

Following him in the list of victories is Roger de Vlaeminck, with 11 monument wins, 3 times in San Remo, a single Flanders, and another Liege. A couple of victories in Lombardia and no less than 4 wins in the Hell of the North, a race that the Gypsy made his own and still holds the record for victories in Roubaix shared with Tom Boonen.

Rik Van Looy completes this trio with a total of 8 monument victories: 1 Milan-San Remo, 2 Flanders, 3 Paris-Roubaix, 1 Liege, and 1 Lombardia. In his case, it is even more remarkable as he was not a versatile cyclist like Merckx or a pure classics rider like de Vlaeminck. Van Looy was a pure sprinter who accumulated over 400 victories in his career.

Ranking of cyclists with the most wins in the Monuments

Throughout history, the Monuments have served as the ultimate barometer for measuring the greatness of the most well-rounded cyclists. Winning one of these classics is already a monumental achievement, but stringing together victories on different terrains—from cobblestones to major climbs or explosive finishes—is what sets the legends apart from the rest. In this context, historic names continue to dominate the rankings, although Tadej Pogacar, at 27, has already joined the ranks of the greatest and now has only Merckx ahead of him.

1. Eddy Merckx – 19 victories
2. Tadej Pogacar – 12 victories
3. Roger De Vlaeminck – 11 victories
4. Costante Girardengo – 9 victories
5. Fausto Coppi – 9 victories
6. Sean Kelly – 9 victories
7. Rik Van Looy – 8 victories
8. Mathieu van der Poel – 8 victories
9. Tom Boonen – 7 victories
10. Fabian Cancellara – 7 victories

Tadej Pogacar faces a challenge that has never been achieved in cycling

In 2026, the name that could rewrite the history of the Monuments is Tadej Pogacar. The Slovenian arrives at Paris-Roubaix with a dual opportunity that surpasses any other recent goal in cycling.

On one hand, if he secures victory at the Roubaix velodrome, he would complete the full set of Monuments in his career. He would be the fourth cyclist to achieve this and the first in over half a century—a feat that alone would place him in a historic league.

But the stakes go much further. Pogacar can not only close that circle, but he would do so in a season in which he has already demonstrated a breadth of dominance rarely seen. His recent victory in Flanders and the fact that he has finally cracked Milan-San Remo this year have completely changed the game.

If he wins in Roubaix, the schedule would put him in an unprecedented position. He would have three Monuments under his belt in the same season, with Liège–Bastogne–Liège and the Giro di Lombardia still to come. Two races that, given their profile and history, are a perfect fit for his strengths.

At that point, the conversation would shift away from simply completing the five Monuments over the course of a career. The conversation would shift to something that has never happened in this sport: winning all five Monuments in a single year.

Not even Eddy Merckx, the sport’s all-time great, achieved anything like that. The Belgian did manage to string together seasons with three Monuments, but he never achieved the full set in a single year. Pogacar, on the other hand, has already demonstrated a unique ability to perform at the highest level on any terrain and throughout the entire calendar.

Furthermore, his recent consistency reinforces that possibility. Last season, he was able to reach the podium in all five Monuments, something no other rider had achieved until now. That consistency, combined with his ability to win on both explosive courses and in high-mountain finishes, makes him the only current cyclist with a realistic profile to aspire to that challenge.

The big question right now remains Roubaix. The terrain isn’t the most favorable for a rider with his profile—lighter and more accustomed to making his mark on climbs. However, his progress on the cobbles and his competitive drive have dispelled many of the doubts that existed just a few years ago.

If he manages to overcome that hurdle, cycling will enter completely new territory. It won’t just be about joining an exclusive club, but about redefining what is possible within the Monuments.