Analysis | How Milano–Sanremo is won: sprint, long-range attack, on the descent, Cipressa, Poggio…

Although in recent years race strategy has been shaped by UAE’s brutal pace on the Cipressa and Tadej Pogacar’s repeated digs at Mathieu van der Poel, historically Milano–Sanremo has been the most unpredictable Monument on the calendar, and its finales have evolved clearly from 1982 to today. We review the past decades with the help of an infographic by our colleagues at Spiegone Ciclistico.

In the 1980s, the race offered a broader range of scenarios. Wins could come from long-range moves, late attacks in the final kilometres, or even from the Cipressa. In 1982, for instance, Marc Gomez won after an attack on the Poggio descent, a formula later repeated by riders such as Moreno Argentin or Laurent Fignon. That variety reflected a less controlled era, with less structured teams and more room for individual initiative.

One key point has been the Cipressa, 5.6 kilometers at just over 4%, a climb that ends within the final 10% of the 300-kilometer long monument. However, it has only rarely proved decisive. The clearest example is Gianni Bugno in 1990, who attacked there to anticipate the favourites. Despite its relative difficulty, the Cipressa has seldom made a definitive selection, largely due to peloton control and the challenge of holding an advantage all the way to Sanremo.

The Poggio di Sanremo, by contrast, has become the decisive battleground. From the late 1980s and especially through the 1990s, many winners forged victory on this climb. Riders like Claudio Chiappucci, Maurizio Fondriest, and Gabriele Furlan used this point to split the race. More recently, names such as Vincenzo Nibali in 2018 or Mathieu van der Poel in 2023 showed the Poggio remains the ideal springboard for winning moves.

Beyond the climb, the Poggio descent has played a key role in several editions. It is a technical run-in that allows gaps to open if riders are willing to take risks. In 2022, Matej Mohoric produced a stunning descent to seal his attack made memorable also by the use of a seat drop post on his bike. These outcomes show that climbing power is not the only determinant; technical skill matters too.

Another crucial phase is the final two kilometres, where some riders have struck late. Cases like Fabian Cancellara in 2008 or Filippo Pozzato in 2006 prove that, even after the Poggio, it is still possible to avoid a sprint if the timing is perfect. However, this avenue has become less frequent over time.

The sprint, whether from a small group or a large bunch, gained prominence across the last decades up to the mid-2010s. The trend towards tighter team control favoured sprint finishes and wins by riders like Óscar Freire. In 2016, Arnaud Démare prevailed from a large sprint, the last time it finished that way. In any case, the reduced sprint of a small group is the most common outcome, especially when Poggio attacks drop the pure fast men.

In recent years, the race has taken a new turn. More complete riders have lifted the pace on the Cipressa, hardening the race before the Poggio. Teams with marquee leaders have applied more aggressive strategies, reducing the chances of traditional sprinters. Mathieu van der Poel’s 2023 win with an attack on the Poggio, or Matej Mohoric’s 2022 success with a fearless descent, reflect this modern trend.