San-Remo, Roubaix and the two puzzles Tadej Pogacar still has to solve

By the end of the 2025 season, his record in the monuments had begun to look almost unreal. Ten victories across three different races, podium finishes in all five in the same year, and a place on the all-time list behind only Eddy Merckx (19 wins) and Roger De Vlaeminck (11 wins).

What Pogačar does not yet have is the complete set. Milan-San Remo and Paris-Roubaix still sit blank in his monument album, guarded for now by Mathieu van der Poel, who beat him on the Via Roma in March and again over the cobbles in April. The Slovenian has made little secret of his desire to finish the collection and join Rik Van Looy, Eddy Merckx and Roger De Vlaeminck in that rarest of clubs.

The 2025 campaign showed that the ambition is realistic in broad terms. Pogačar is already competitive at all five. Winning Flanders, Liège and Lombardia might almost feel like routine. Beating Van der Poel at San-Remo and Roubaix in the space of one spring looks far more complicated.

It is entirely possible that Milan-San Remo continues to slip from Tadej Pogačar’s grasp for as long as Mathieu van der Poel is on the start list. In 2025, the Dutchman simply refused to be dislodged. He rode into the red to follow Pogačar’s vicious accelerations on the Cipressa, survived the Poggio, and still had enough left to win on the Via Roma, with Filippo Ganna bridging back and stealing second while Pogačar had to settle for third.

The problem for Pogačar is not creating damage on the climbs. He has already bent the race away from its traditional pattern, where everything waits for the Poggio. 

The problem is shaking a rider who can match his accelerations almost stride for stride, then finish faster on the flat. As long as Van der Poel can ride his wheel over both the Cipressa and the Poggio, Milan-San Remo will tilt 9 out of 10 times in the Dutchman’s favour.

But there might be hope for Pogačar yet. In the chaos on the Cipressa this year, Van der Poel’s grimace suggested he was right on his limit. Little wonder, given that UAE Team Emirates had lit the fuse from the foot of the climb through Tim Wellens and Jhonatan Narváez, before Pogačar launched and dragged the Cipressa under the symbolic nine minute mark.

“Well, the plan was for me to go full from the bottom,” Wellens said afterwards. “Then Isaac Del Toro would take over. Jhonatan Narváez would sit on Tadej Pogačar’s wheel and let the gap open.” Somewhere in that blueprint may lie the solution. 

In 2025, Del Toro was nowhere to be seen on the Cipressa, but his results since have shown an explosiveness not far off Pogačar’s own. He might yet prove to be the missing piece the Slovenian needs. One extra carriage in the UAE train on the Cipressa Express could be enough to push van der Poel those few percentage points deeper into the red and finally make him crack.

And then there is another name who could shape the way the race unfolds: Remco Evenepoel. The 25-year old Belgian has hinted he may line up at the 2026 edition and showed in the autumn, at the European Championships, the World Championships and Il Lombardia, that he is the one who can come closest to Pogačar in one day races without ever quite tipping over into genuine danger.

After Il Lombardia, Evenepoel was crystal clear about what needs to happen next. “It’s not about one minute power. We’re already going full gas before that. It’s about sustaining that intensity for three to five minutes. I worked on it in the summer, and I feel I’m getting better, but this winter we’ll need to really focus on it.”
 
If Evenepoel manages to take that next step, he could become a crucial ally for Pogačar against Van der Poel, not least because it is hard to imagine any scenario where Evenepoel would not work with him in a long range move if the pair slipped clear and Van der Poel was caught on the wrong side of a split. 

And even though Evenepoel’s sprint has improved markedly, Pogačar would still be the safer bet if both of them reached the Via Roma together, a scenario where this box on the Slovenian’s palmares might finally be ticked on his fifth appearance at the race.

Milan-San Remo may already be a fascinating challenge, but the "Hell of the North" is an even more intriguing proposition for Pogačar. Where the other monuments offer proper climbs to make the difference, Paris Roubaix offers cobbles, and that is not something that, at least on paper, should suit the 66 kilo Slovenian from a physiological point of view.

In 2025, Pogačar took the start there for the first time, accepting the risks that come baked into the race with the reluctant blessing of team manager Mauro Gianetti. And Pogačar would not be Pogačar if he did not immediately leave an impression. 

With more than 100 kilometres to go he was already shaking the tree, and on the famed Trouée d’Arenberg he and Mads Pedersen were the only riders able to follow Mathieu van der Poel.

After a flat tyre for Pedersen, the race distilled into a straight head to head between Van der Poel and Pogačar, with both riders seemingly evenly matched. 

With 39 kilometres remaining, Pogačar tried to shed the faster finishing Van der Poel by accelerating on the sector of Pont Thibault à Ennevelin, only to misjudge a right hand bend. That error handed Van der Poel a gap of around 20 seconds, and he never looked back.

What lingered, though, was the realisation that Tadej Pogačar is perfectly capable of riding the cobbles with the very best, and even of putting them under pressure.

So what to expect in 2026? Where Pogačar may still have cards to play in San Remo, he seems to hold far fewer in Paris-Roubaix. There appears to be no realistic scenario in which he can crack Van der Poel on the cobbles, leaving a sprint on the Roubaix Vélodrome as the best he can reasonably hope for.

And yet there is one card every rider keeps close to their chest in Paris Roubaix, and her name is Lady Luck. More than perhaps any other race, fortune and misfortune shape the final outcome but, as the saying goes, you make your own luck.

So if Pogačar wants to maximise his chances of success, he first has to minimise his exposure to bad luck. That means getting himself into a mano a mano fight with Van der Poel as early as possible, with perhaps Mads Pedersen and Wout van Aert for company. The fewer riders around him, the fewer opportunities there are for crashes or tactical games to create the kind of chaos that can turn the result on its head.

For UAE, the tactical recipe on the Hell of the North is therefore brutally simple: make the first hours as hard as possible, launch early, really early, and then trust that the gods of Roubaix might look kindly on Pogačar.

Winning all five monuments over the course of a career is already a rarity, with only three riders in history having managed it. To win them all in a single season is something else entirely.

To get there, the key lies in the roulette of Roubaix. That is by far the least likely of the five and, more than any other, feels like something outside Pogačar’s control. In Milan-San Remo, by contrast, a fully tuned UAE train could materially increase his chances of victory, and that has to be seen as a far more realistic scenario.

Then there are the three monuments Pogačar has already made his own, each of them more than once: the Tour of Flanders, Liège-Bastogne-Liège and Il Lombardia. In the latter two in particular he has been utterly dominant in recent years, and it feels as though only a significant step forward from Remco Evenepoel at Red Bull–BORA–hansgrohe could seriously alter that balance.

In his Tour of Flanders appearances, the Slovenian boasts a near-perfect record, with two wins from three starts, but even if both victories came by way of a solo, they feel less overpowering than his displays at Liège-Bastogne-Liège and Il Lombardia. A peak Van der Poel, something we did not see in 2025 in Flanders because of illness, would have to be considered a serious threat here.

So can Tadej Pogačar win all five monuments in 2026? The odds say no. He has to win a race where so much depends on everything but himself, engineer another where absolutely everything has to fall into place to crack Van der Poel, and then pass unscathed through three more monuments without the slightest interruption from illness or injury.

But then again, Tadej Pogačar is Tadej Pogačar...