The five best editions of Milan-Sanremo in the 21st century

This was a remarkable edition of Milan-Sanremo. For the first time since 1996, the race was effectively decided by an attack on the Cipressa, something that had not happened at all in the 21st century.

Much of the race revolved around Tadej Pogačar’s determination to win La Primavera. The Slovenian has already won three of cycling’s five Monuments: the Tour of Flanders, Liège Bastogne Liège and Il Lombardia, leaving Milan-Sanremo as one of the major prizes still missing from his collection.

For Pogačar to win Milan-Sanremo, the race needs to be extremely hard. Since 2022, UAE Team Emirates-XRG has repeatedly tried to shape the race in that direction. That year the team set a fierce pace on the Cipressa, but it was not selective enough. 

Matej Mohorič then launched a daring attack on the Poggio descent, using a dropper seatpost to maximise his speed downhill. Even after dropping his chain in the final kilometre, he managed to fix it and sprint to victory.

In 2023, the Cipressa again failed to split the race sufficiently. On the Poggio, Tim Wellens drove the pace before a group featuring Filippo Ganna, Mathieu van der Poel, Tadej Pogačar and Wout van Aert went clear. Van der Poel attacked near the summit and rode solo to victory, while Pogačar finished fourth.

UAE tried to make the race harder again in 2024, but the team ran out of riders before the top of the Cipressa. On the Poggio, Pogačar attacked and only Van der Poel could follow. However, with teammate Jasper Philipsen in the chasing group, Van der Poel refused to work, and the duo was caught. Philipsen went on to win the sprint, while Pogačar finished third.

In 2025, UAE finally executed the perfect Cipressa leadout, reducing the peloton to a small group and allowing Pogačar to attack on the climb. Only Van der Poel, Filippo Ganna and Romain Grégoire could initially respond, although Grégoire soon dropped away.

Pogačar pushed the pace hard on the Poggio and dropped Ganna, but once again he could not distance Van der Poel. The Italian time trial specialist fought his way back before the finish on Via Roma, but in the three rider sprint Van der Poel proved fastest. Pogačar had to settle for third yet again.

What does Pogačar need to finally win Milan-Sanremo? A tailwind would certainly help, but more importantly the race must be extremely selective before the Poggio. If UAE can reduce the race to a small group and launch Pogačar from a very high pace, it might finally be enough to distance Van der Poel.

Executing such a plan, however, is far from easy. And for now UAE may lack the full strength required, with Brandon McNulty out after crashing in Paris Nice, Jhonatan Narváez injured earlier in the season, and Tim Wellens sidelined with a broken collarbone.

The 2013 edition of Milan-Sanremo may well have been the most legendary in the race’s modern history. The day began with rain, which soon turned to hail and eventually heavy snowfall. Under today’s weather protocols the race would almost certainly have been stopped, but the riders battled on through some of the harshest conditions ever seen in a Monument.

By the time the peloton reached the Passo del Turchino, the situation had become extreme. A thick layer of snow covered the road and several riders were visibly struggling, some even in tears on the bike. Eventually the race was neutralised, with riders taking refuge in their team buses before the race restarted roughly 50 kilometres further down the route.

Not everyone returned to the start line. Several riders, including Tom Boonen, chose not to continue in protest against the conditions. Others simply could not cope with the brutal weather, with strong riders such as Edvald Boasson Hagen and Thor Hushovd abandoning.

The unusual circumstances created a chaotic and unpredictable finale. Philippe Gilbert launched a surprising attack on the flat between the Cipressa and the Poggio, a move rarely seen from the reigning World Champion. He was joined by riders including Fabian Cancellara, Sylvain Chavanel, John Degenkolb and Filippo Pozzato.

From that group, Ian Stannard, Eduard Vorganov and Chavanel went clear. Behind them, Luca Paolini attacked on the Poggio and bridged across alongside Pozzato, Cancellara, Gerald Ciolek and Peter Sagan. The Slovak eventually closed the gap to the leaders on the descent, setting up a six rider battle for victory.

Sagan appeared the overwhelming favourite, but the brutal weather had made the race unpredictable. Launching the sprint early on Via Roma, he seemed on course for victory, only for Gerald Ciolek to surge past from his slipstream and take a famous win. Sagan finished second, with Cancellara completing the podium in one of the most extraordinary editions of Milan-Sanremo.

This edition was already mentioned briefly in the discussion of the 2025 race, but it deserves a closer look. Matej Mohorič had already built an impressive record at Milan-Sanremo, finishing in the top ten five times and narrowly missing it with an 11th place in 2021.

Yet victory had always eluded him. Knowing he was unlikely to drop the favourites on the Poggio itself, Mohorič looked for another way to win. With the finish on Via Roma coming shortly after the Poggio descent, he realised the downhill could offer a decisive opportunity.

To maximise his advantage, the Slovenian equipped his bike with a dropper seatpost, allowing him to lower his saddle at the push of a button. The lower position improved both stability in the corners and aerodynamics, giving him an edge on the technical descent.

At the summit of the Poggio, Søren Kragh Andersen, Mathieu van der Poel, Tadej Pogačar and Wout van Aert held a small advantage. Moments later, Mohorič launched himself into the descent in spectacular fashion. Taking enormous risks through the corners, he quickly caught and passed the leading group.

Before the race he had jokingly asked whether Sanremo had a good hospital, a sign of how far he was willing to push the limits. Fortunately he stayed upright. Even dropping his chain inside the final kilometre could not stop him, as he managed to fix it mid ride before sprinting to victory on Via Roma.

The daring move instantly became one of the most memorable moments in Milan-Sanremo history and remains the biggest win of Mohorič’s career.

The 2003 edition of Milan-Sanremo may have been the clearest example this century of a rider simply being the strongest in the race. Paolo Bettini attacked on the Cipressa, with only four riders able to follow. When the group hesitated to cooperate, Bettini accelerated again and dropped them on the flat section between the Cipressa and the Poggio.

However, just before the Poggio the race came back together. Normally that would signal the end of a rider’s chances, especially after such a long effort. While Bettini had already spent significant energy, the peloton behind him was still relatively fresh.

But Bettini was no ordinary rider. On the Poggio he once again followed the decisive moves and reached the finish in a small leading group. In the three rider sprint on Via Roma, he won comfortably.

Winning Milan-Sanremo is notoriously difficult, even for the strongest rider in the race. Bettini seemed to defy that logic. Despite spending much of the race on the attack, he still had the power to finish the job, a reminder that on his best days the Italian was simply unbeatable.

Another edition of Milan-Sanremo with a thrilling final. Just after the Cipressa descent, Van Avermaet, Offredo, O’Grady, and Chainel rode away. They started the Poggio with a 32“ bonus. On the Poggio, Van Avermaet attacked at a super smart moment, in the slipstream of a passing car. He directly dropped the whole group and went solo. It's not like the others didn't try; they just couldn't follow. 

In the peloton, attacks were flying. However, nobody got away, like most times on the Poggio, so the pace constantly dropped. It looked like Van Avermaet couldn't lose the race anymore, a perfect situation for him. Then, Nibali attacked at a smart moment and got away. The Belgian reached the summit of the Poggio first, a little over 10" before Nibali, with O'Grady and Offredo on his wheel. 

Chainel couldn't follow the Italian. The best riders of the peloton: Cancellara, Ballan, Gilbert, Pozzato, Goss, Scarponi, and Marcato joined them just before the descent. Shortly after, in the descent of the Poggio, the latter slid out and crashed out of the group.

However, after the descent was finished, Van Avermaet got caught. Attacks started flying. Offredo attacked, then Gilbert went, then Gilbert went again, but they got caught every time. Nobody was a match for Goss in the sprint. Gilbert got 3rd even though he attacked twice just before the sprint. This would be the best result he ever got in Milan-Sanremo, together with his 3rd spot in 2008, his only missing monument.