Tadej Pogačar’s Milan-San Remo Quest: Can He Finally Conquer La Primavera?
Updated March 17, 2026
Tadej Pogačar, one of cycling’s most dominant forces, is set to challenge for Milan-San Remo once again. While his success across numerous races is undeniable, this particular monument continues to elude him. This year’s edition, taking place on Saturday, March 21st, will observe Pogačar attempt to break the mold and secure victory in a race that has historically resisted his explosive style.
The Challenge of Milan-San Remo
Milan-San Remo is unique in its length and relatively flat terrain, culminating in a dramatic finale. For decades, the race has followed a predictable script: a fast peloton, a decisive move on the Poggio climb (5.5km from the finish), and a sprint for the line on Via Roma. This formula has crowned a diverse range of champions – sprinters, classics specialists, and opportunists alike.
But, this traditional scenario doesn’t favor Pogačar’s strengths. He thrives on aggressive attacks and sustained power, but a bunch sprint on the Via Roma significantly diminishes his chances.
The Cipressa Gambit
In the 2025 edition, Pogačar deviated from convention, launching a powerful attack on the Cipressa climb, approximately 17km from the finish. This move, unprecedented in modern San Remo racing, disrupted the peloton and created a leading group of three – Pogačar, Mathieu van der Poel, and Filippo Ganna. While the tactic proved effective in creating separation, Van der Poel ultimately emerged victorious, leaving Pogačar to settle for third place.
Pogačar now faces a dilemma. He knows that waiting for the Poggio risks a bunch sprint, but his rivals are aware of his Cipressa strategy. He must find a way to surprise them and drop them before the final climb.
A Novel Ally: Isaac del Toro
This year, Pogačar will rely on the support of UAE teammate Isaac del Toro, who has been in excellent form with victories at the UAE Tour and Tirreno-Adriatico. Del Toro’s role will be crucial in setting the pace and launching attacks to soften up the peloton before Pogačar makes his move. However, UAE Emirates-XRG will be without Jonathan Narváez and Tim Wellens due to injuries.
A Bruised and Battered Peloton
Several key contenders will be absent from this year’s race due to injuries. Mads Pedersen, Michael Matthews, Neilson Powless, and Olav Kooij are among those who will not be competing, potentially opening the door for other riders to challenge for the win. Mathieu van der Poel, however, appears to be in formidable condition.
Forecasters predict crisp spring racing conditions with onshore cross-head winds, which could make the final stretch from the Cipressa to Via Roma even more challenging.
The Equation for Victory
Pogačar understands that to win Milan-San Remo, he must avoid a bunch sprint at all costs. He needs to drop his rivals, particularly Van der Poel and Ganna, before the race reaches the Poggio. A repeat of his Cipressa attack remains the most likely path to success, but he will need to be prepared for his opponents to anticipate and counter his move.
Milan-San Remo is often described as the easiest monument to finish but the hardest to win. For Pogačar, this year could represent his best opportunity to finally conquer La Primavera and complete his collection of cycling’s most prestigious one-day races.