ANALYSIS: Which of Tadej Pogacar, Mathieu van der Poel, or Remco Evenepoel can win all 5 monuments?

Tuesday, 25 March 2025 at 20:00

Mathieu van der Poel’s breathtaking win at the 2025 Milano-Sanremo, perhaps the greatest edition in modern history, was more than just another victory. It reignited one of cycling’s most intriguing debates: of the three modern kings of one-day racing—Tadej Pogacar, Mathieu van der Poel, and Remco Evenepoel, who is most likely to win all five Monuments?

To date, only three riders in the history of the sport, Eddy Merckx, Rik Van Looy, and Roger De Vlaeminck, have completed cycling’s ‘Grand Slam’ of Monuments: Milano-Sanremo, Tour of Flanders, Paris–Roubaix, Liège–Bastogne–Liège, and Il Lombardia. Now, with 17 of the last 20 Monuments, World Championships or Olympic Games won by just Pogacar, Van der Poel, or Evenepoel, the question is no longer if someone will attempt the feat, but who will actually pull it off.

The stats

Since the start of 2022, only six different riders have won either a Monument, a World Championship, or an Olympic Games road race. Just three, Matej Mohorič, Dylan van Baarle, and Jasper Philipsen, have interrupted what has essentially become a cycling trinity.

Van der Poel, Pogacar, and Evenepoel have not only dominated the biggest races, they’ve done so in entirely different ways: brute strength, solo brilliance, tactical genius, and mind blowing endurance. And yet, as dominant as each of them has been, the ‘complete set’ of Monument victories remains elusive.

Tadej Pogacar

Let’s start with the obvious frontrunner. Tadej Pogacar is, quite simply, one of the most complete riders cycling has ever seen. He has the tactical intelligence, raw climbing ability, and endurance to win on any terrain. His palmarès already reflects that. He is the only active rider to have won a Monument on the cobbles (Flanders), in the Ardennes (Liège), and in the mountains (Lombardia). He has even won from sprints and solo attacks.

Only Milano-Sanremo and Paris-Roubaix remain. And neither appears out of reach.

Tadej Pogacar defies what is possible as a cyclist

Milano-Sanremo, despite its reputation as a “sprinters' classic,” has become increasingly open to puncheurs and attackers. Pogacar has already come close here, most recently forcing a Cipressa selection that smashed a decades-old climbing record. “We are seeing new tactics succeed,” analysts noted after this year's edition. Had it not been for Van der Poel’s perfect timing and Filippo Ganna’s inspired ride, Pogacar might already have ticked this one off.

The flip side to this argument is that Saturday showed just how hard Milano-Sanremo is for Pogacar, essentially because it’s not hard enough. Try as he might, Pogacar could not distance Van der Poel on the poggio, and he lost the race there once again.

Then there's Paris-Roubaix, the elephant in the room for climbers. But is Pogacar really just a climber? In 2022, he rode the cobbles of the Tour de France like a veteran. He has never tested himself fully at Roubaix, but his engine, power output, and bike handling are elite-level. Even Van der Poel believes Pogacar will win the race one day, but will that come this spring or in the future?

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That final caveat may be the key. If he targets Roubaix with the same focus he gave Flanders, the outcome may well be the same. But, will someone with GC ambitions in the Tour in July be prepared to risk it all on the cobbles in Roubaix?

Verdict: Let’s get one thing straight, Pogacar is the most likely to win all five Monuments, not only because he is closest, but because nothing in cycling seems beyond him.

Mathieu van der Poel

There is no doubt that Van der Poel is one of the most gifted and captivating riders of his generation and in fact of all time. His seventh Monument at Milano-Sanremo 2025 confirms what many already believed: he’s a once-in-a-lifetime talent. Add in seven cyclocross world titles and mountain biking success, and he has one of the most diverse records in modern cycling.

But the road to five Monuments is not just about greatness, it’s about versatility.

Van der Poel still needs to win Liège–Bastogne–Liège and Il Lombardia. Neither of these is beyond his reach, but they are undoubtedly the toughest fit for his style. They’re typically dominated by climbers and puncheurs, riders like Pogacar and Evenepoel, especially in recent years.

Was Mathieu van der Poel's second Milano-Sanremo win his greatest?

Even Van der Poel himself is realistic: “Winning Liège and Lombardy seems impossible to me if Pogacar and Remco Evenepoel are at the start,” he told La Dernière Heure. “It’s not just about thinking about winning the five Monument Classics, but also about which riders you will face in the race.”

Yet he does believe it’s possible: “It would certainly be nice to be able to win the five Monuments, but I know I have already won a lot and I can think about moving this objective forward.”

Van der Poel has the power, and his descending and technical skills are second to none. But to win Liège or Lombardia, he may need the stars to align, or hope Pogacar and Evenepoel skip those editions.

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In reality, Van der Poel’s next quest for greatness may come on a mountain bike later this year, as he aims to add another rainbow jersey to his extraordinary collection.

Verdict: He has the class and ambition, but winning the hilly Monuments would require perfect preparation, course tailoring, and perhaps a weakened start list. Less likely than Pogacar, but not impossible.

Remco Evenepoel

On paper, Evenepoel has the most ground to make up. He’s never won a cobbled Monument, and has yet to seriously contest Milano-Sanremo. But if there’s one thing we've learned about Evenepoel, it’s to never rule him out when the terrain suits his raw power and aggressive racing style

He already has back-to-back wins at Liège, the 2022 World Championship, and 2024 Olympic gold, all won with dominant, long-range attacks. Few can match him when he gets 30 seconds of daylight.

We are still waiting to see Remco Evenepoel in 2025

Let’s cast our minds back to the Olympic road race in Paris last year. People quickly forget how incredible the Belgian was on that day, I would go as far to say that even Pogacar would have struggled to snatch the gold medal from him then.

But the problem is Paris-Roubaix and Flanders, races that don’t allow for the kind of controlled, solo effort he thrives on. Evenepoel is yet to have proven himself capable of winning on the cobbles as Pogacar and Van der Poel can, and does he lack some of the raw power of someone like Mathieu van der Poel and Wout van Aert?

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He also lacks a finishing kick in group scenarios when compared to some of the bigger riders, which makes races like Sanremo difficult unless he arrives solo, which, as Van der Poel has proven, is no easy task.

Still, Evenepoel is only 25. His tactical awareness improved massively in 2024, and he is clearly aware of his place in cycling history. He’s a student of the sport and may one day shape his entire season around attempting to complete the set.

Verdict: A long shot for all five, but not out of the question. If anyone can rewrite their own limits, it’s Remco.

Three great riders, one historic goal

The ambition to win all five Monuments once seemed like a relic of cycling’s golden age. But thanks to Van der Poel, Pogacar, and Evenepoel, it’s now a living question.

It almost seems wrong to not have truly mentioned Wout van Aert so far, but for all his incredible ability he still has just one monument win to his name. That’s a shame, as he may have the best all-round profile to complete the set, judging by his climbing ability we have seen in the Tour.

Pogacar is the most complete and the closest to achieving it. If he targets Roubaix, he can win it. Sanremo will continue to be unpredictable, but he’s been on the cusp multiple times.

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Van der Poel’s versatility, brilliance, and tactical instinct make him a contender in almost any race, but climbing-focused classics remain a challenge.

Evenepoel, for now, remains the outside, but perhaps the one with the most upside if he evolves his style.

Who will be the first to join cycling immortality as the next winner of all five Monuments?

Right now, the smart money is on Pogacar.

But as we’ve seen time and time again with this trio, expect the unexpected.

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2 Comments

slappers66 26 March 2025 at 15:09+ 255

MSR really did open the can of worms.... A personal view, of the three noted Tadej is most likely to get the set he has the skill, the talent and sheer bloody-mindedness to win everywhere. Yes the it'll all have to come right to pick up Roubaix and MSR but he's already proved himself on all terrain. I'd rate Remco's chances of getting the 5 fractionally higher than MVDP, he can climb so LBL/Lombardia as less of a problem but he's yet to prove himself on the other races and we don't know how well and how quick he'll get back to where he was after injury, this has been a long lay off. MVDP, I'd love to see him do it but I think Lombardia is too much of a stretch, the organisers will not create an "easier" route just to pull him in. I've said on other articles that I fear for Wout, I don't know that he is at the same level as MVDP and Tadej anymore, they have cranked the level up while Wout has been recovering from last years debacle. Will it happen who knows but it's going to be incredible to watch over the next couple of years!

Mistermaumau 26 March 2025 at 15:07+ 3743

Quite true but I’d not rule MVDP out yet, am pretty sure he will still improve in climbing and maybe not every rival will do every edition so stars may still align. Ironically, all three and even Wout, would probably (at least 2 definitely) win all 5 if it wasn’t for the others.