Milano-Sanremo on March 21, 2026, presents Tadej Pogacar with the same tactical puzzle that has resisted him before. The Slovenian remains one of the strongest riders in the world, but this Monument does not finish on the climbs where his attacks usually succeed. Instead, the race ends on the Via Roma in Sanremo after nearly 300 kilometers, with the Cipressa and Poggio placed too late and too shallow to guarantee selection. Mathieu van der Poel remains the rider most capable of beating him if the race comes down to positioning and timing in the final kilometers.
The unique nature of the Classicissima explains why. Unlike the Tour of Flanders, Liege-Bastogne-Liege, or Il Lombardia, Milano-Sanremo does not feature the extreme climbs that usually make Pogacar’s attacks so devastating. The Cipressa sits 25 kilometers from the finish, long enough to be painful but not steep enough to shed the best positioned sprinters. The Poggio comes with six kilometers remaining, a short twisting climb where attacks can succeed only if the descent is ridden with absolute commitment. Most years, the race regroups before the final straight, and the winner is decided by who held the best wheel through the chaos.
How Will the Race Be Won?
The race will be won by reading the moves on the Poggio and holding position through the descent into Sanremo. Pogacar will need to attack early enough on the climb to build a gap before the summit, or he will need a teammate strong enough to control the pace and prevent the race from coming back together. That is where Isaac del Toro could prove crucial, offering the kind of sustained climbing support that Pogacar has rarely had in this race. If the Slovenian cannot break clear on the Poggio, the finish favors Van der Poel, who has the acceleration and tactical instinct to win from a reduced sprint.
What If the Favorites Cancel Each Other Out?
If Pogacar and Van der Poel mark each other too closely, the race opens for a late attacker or a surviving sprinter. Arnaud De Lie has the endurance to survive the coastal climbs and the speed to win if he reaches the Via Roma in a small group. Filippo Ganna remains relevant if he can stay with the pace over the Cipressa, though his chances depend on the race staying together longer than Pogacar would prefer. The finish is a slight uphill drag, which rewards riders who can accelerate out of the final corner with momentum already built.
Watch for the move on the Poggio. If Pogacar goes early and commits to the descent, the race will be decided in the final four kilometers. If he waits, or if Van der Poel covers him cleanly, the sprint will come down to who held the best position through the final corner. Either way, this is the Monument that rewards patience as much as power, and the rider who solves that problem first will reach Sanremo alone.