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Will Tadej Pogačar ever win Milan-San Remo?
Not many people can say a near-300km Monument is ‘too easy’, but for Tadej Pogačar at Milan-San Remo, that feeling is all too real.
The world champion thrives on the toughest climbs, in the most punishing conditions, whether it’s on gravel or cobbles, on a 100km attack or a kick to the line, but at La Classicissima he just can’t get clear and doesn’t quite have the finishing sprint.
After his incredible attack last weekend only netted him a third place finish, it begs the question: will Pogačar ever win Milan-San Remo? Below, we’ll look at his problems and the potential solutions.
The parcours
Pogačar has raced Milan-San Remo five times, finishing 12th in 2020, 5th in 2022, 4th in 2023 and 3rd in both 2024 and 2025. That’s a pretty good record for most, but Pogačar races for victories, and the race parcours is holding him back with its largely flat profile until the final two climbs, meaning he only really has two opportunities to make his mark.
The Cipressa
His first chance is on the Cipressa, 5.6km long with an average gradient of only 4.1% with its steepest section coming just past the halfway point. In order to get a gap on the faster finishers around him, that 9% pitch is where he needs to make his mark.
No one has won Milan-San Remo from an attack on the Cipressa since Gabriele Colombo in 1996 but it had been widely suggested that Pogačar would try his luck this year, so it was little surprise to see him go on the offensive.
Pogačar first launched his attack after a powerful leadout by teammates Tim Wellens and Jhonatan Narváez. That was in the final 3km of the climb, the aforementioned steepest point where the gradient tips towards 9%, and the move brought the race down to a selection of just Pogačar, Mathieu van der Poel and Filippo Ganna. He would hit out again and again and again, but Van der Poel answered each time and Ganna fought his way back despite being dropped.
Pogačar set a new record time up the Cipressa, taking just 8min 59sec to reach the top according to his Strava, but that still wasn’t enough to get rid of his two companions.
The Poggio
Following the descent of the Cipressa there’s a long flat section to survive before the Poggio, which peaks 7km from the finish line.
The Poggio is only 3.7km long at a 3.7% average, but this climb and its technical descent have worked as successful launchpads to many Milan-San Remo victories over the years.
In 2024, Pogačar himself tried to follow suit by breaking away 200m from the summit, only to be reined in by that man Van der Poel and engulfed back into the main group on the descent. And once that had happened he was always going to be out-gunned by a sprinter like Jasper Philipsen in the run to the finish on the Via Roma.
Pogačar set the Poggio KOM with that effort, but as with his effort on the Cipressa this year, it wasn’t enough. The climb is just not a big or hard enough climb to get a big enough gap. He knows as much too, admitting to Cycling Pro Net this year that he ‘would prefer the Poggio to be 5km longer at 10%. It’s a really hard race for me to make a difference, so yeah, the law of physics is playing here and I cannot do magic.’
The Via Roma
Pogačar is a strong sprinter, but not quite on the level of true Classics specialists such to Van der Poel. In recent years he’s missed out on wins at Milan-San Remo (twice), E3 and the Tour of Flanders because he couldn’t come out on top in small group sprints.
Realistically, to get a result from a small group at Milan-San Remo, he’d need to find a way to drop Van der Poel, Ganna and Wout van Aert beforehand, which as recent years has shown is no easy task.
But outside of relying on them to simply not turn up, what more can Pogačar do?
The team
In a video posted by UAE Team Emirates after this year’s Milan-San Remo, the team showed what their plan had been for the day – to approach the Cipressa, set the new best time, and attack. After the line, an exhausted Pogačar simply said, ‘I couldn’t do more.’
Given that the race route isn’t changing, could UAE Team Emirates have had more bodies than just Wellens and Narváez to support Pogačar on the Cipressa? With a squad as strong as UAE’s, that’s surely possible – in fact, Isaac del Toro was actually meant to be pulling between Wellens and Narváez, but wasn’t in a position to do so. Would that extra push before Pogačar’s attack have been enough?
Expect there to be at least more rider pulling on the Cipressa in 2026.
Will Pogačar ever win Milan-San Remo?
The reality is, when it comes to ticking off his career goals, Pogačar is like a dog with a bone. He will keep on trying to win this race – there’s absolutely no doubt about that. And he has consistently shown that he learns from his losses too, so it’s almost a certainty there will be tweaks made to the strategy next year.
What this year made clear was that until he finds a way to drop Van der Poel, the final sprint will be Pogačar’s downfall every time. A loss in a fast finish accounted for 24% of his defeats between 2023 and 2024. But whether it comes next year or further down the line, such is Pogačar’s strength that it’s hard to see a world in which he finishes his career without a Milan-San Remo victory.
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