The Cipressa trap - How Tadej Pogačar could win or lose Milan-San Remo on the key climb

Tadej Pogačar has admitted that winning Milan-San Remo has become an obsession and his biggest rivals are ready to take advantage of that yet again on Saturday.

The Slovenian is dominating professional cycling, winning almost every race he rides in Merckxian style, yet the La Classicissima still eludes him.

Pogačar has won Il Lombardia four times, Liège-Bastogne-Liège twice and the Tour of Flanders once. He has also won Strade Bianche three times, and now an attempt on Paris-Roubaix this year is under debate. Eddy Merckx won Milan-San Remo seven times in just ten rides. While Pogačar has ridden Milan-San Remo four times, the Italian race has escaped his dominance, leaving him more determined than ever to win on the Via Roma.

"Milan-San Remo is the one that is going to send me to my grave… I'm getting so close but it's so far, it's unbelievable," Pogačar admitted to podcaster Peter Attia during the winter, revealing his frustration.

The Milan-San Remo cliche that it is 'the easiest Monument to finish but the hardest to win' stands true, even for Pogačar.

His exuberant style of racing and his overly aggressive nature means he usually dominates races. But his talents can become his weaknesses in Milan-San Remo, where tactics and race craft are often more important than brute force and natural talent.

Pogačar wears the rainbow jersey but the world champion is rarely first to the line, perhaps because they are so closely marked. Only five world champions have ever won Milan-San Remo, with Beppe Saronni the last, way back in 1983.

"You can lose Milan-San Remo with every decision you make and only the right decision keeps you in the race," Tom Pidcock told Cyclingnews during Tirreno-Adriatico, perfectly describing how Milan-San Remo is balanced on a knife edge of ability, tactics and instinct.

Pogačar and UAE Team Emirates-XRG are still looking for the perfect combination but are determined to win Milan-San Remo on Saturday as they target a series of Spring Classics this year. Their silence about their ambitions this year is a sign of their serious intentions.

They are no doubt plotting their best race strategy but know that Pogačar has little chance of winning a sprint in the Via Roma. He is fast after a long race but not faster than Jasper Philipsen, Mads Pedersen, Michael Matthews and perhaps even Filippo Ganna.

Pogačar needs a hard race on the Turchino climb, along the coast and then over the Cipressa with 26km to go, to perhaps then make a difference with a solo attack on the Poggio.

His problem is that his rivals know his weakness and are ready to use it against him.

Just like in 2024, if UAE and Pogačar race hard, especially on the Cipressa, it could leave them tired and exposed on the Poggio, when the decisive attacks so often come.

"I do want to give them any tips on how to race, I just wish them good luck…" 2017 winner Michał Kwiatkowski told Cyclingnews at Tirreno-Adriatico, with a smile, a thick dose of irony and tactical enticement.

"To win big races you adapt your tactics and try to take advantage of when riders are under pressure to win. That's what I did in 2017. I knew that Peter Sagan was desperate to win and so I forced Sagan to drag us to the finish. You always have to use small but important details like that.

"We'll see who is under pressure this year and race accordingly. You've got to be smart to win Milan-San Remo."

The Cipressa in under nine minutes

In 2024, sports manager Matxin Joxean Fernández let slip UAE's race strategy, revealing to GCN that Pogačar and his teammates had to ride the Cipressa in less than nine minutes to reduce the Milan-San Remo peloton to just 20 riders.

UAE tried to execute that plan but lacked riders on the Cipressa and started the climb out of position. Alessandro Covi did a long turn and then Isaac del Toro eventually came to the front for the midsection of the Cipressa. But the young Mexican cracked before the summit. Pogačar had to tell Tim Wellens to ease the pace and so his rivals and several fast finishers were able to sit on the wheels and get a free ride to the Poggio.

Wellens led Pogačar out on the Poggio but Mathieu van der Poel and other riders were able to follow his first attack and another near the summit.

The Dutchman then chased down the late attacks in the final two-kilometre flat roads to set up Jasper Philipsen to win the sprint. Pogačar came through late to finish a close third but he considered it a defeat rather than a podium success.

"As a team, we changed this race a little bit in the last few years and we're trying to make it work," Pogačar said last year of the team's Cipressa tactic.

"When you bring something new to a race, it's hard to execute it, especially in this kind of race, but every year we put a little bit more work into it a little bit more per cent falls into place. I think in the next few years we can do even better."

The 2024 UAE Team Emirates Milan-San Remo seven-rider line-up included Alessandro Covi, Marc Hirschi, Brandon McNulty, Domen Novak, Diego Ulissi and Tim Wellens. The 2025 squad is expected to be significantly stronger, with more rouleur muscle.

The entry list line-up for 2025 includes Pogačar, Wellens, Novak, Nils Politt, Jhonatan Narváez and Vegard Stake Laengen. Cyclingnews understands that Isaac del Toro was not expected to ride this year but he was strong at Tirreno-Adriatico riding for Juan Ayuso and could replace the USA's Brandon McNulty, who didn't finish stage 7 of Paris-Nice. Ayuso is targeting the Volta a Catalunya that begins on Monday.

Pogačar climbed the Cipressa in 9:35 in 2024 according to La Gazzetta dello Sport. The plan is to again go under Matxin's magic number of 9:00 and smash Gabriele Colombo's record of 9:19 from 1996 when he attacked, was joined by Max Sciandri, Alexander Gontchenkov and Michele Coppolillo, then got away inside the final kilometre to win alone.

"I wouldn't say a project, but we've already laughed that we're going to do the Cipressa under nine minutes," Wellens admitted at the team's media day in January.

"Milan-San Remo last year was also an example that not everything goes according to plan," he added.

The Cipressa conundrum

Pogačar quickly recovered from his Strade Bianche road rash and trained at home in Montecarlo while most of his rivals raced Paris-Nice or Tirreno-Adriatico and suffered in the cold and rain. He is expected to do a final recon ride of the final kilometres of Milan-San Remo before travelling to Milan on Thursday.

Pogačar has no doubt been thinking about his Milan-San Remo strategy this week and a similar race scenario to Colombo's victory would be great for him.

A solo attack would be far too audacious even for Pogačar. Still, if a select group got away, without some of the big-name favourites, it would improve Pogačar's chances of attacking alone on the Poggio and then his chances of winning Milan-San Remo.

The Cipressa starts 21.7km from the finish of Milan-San Remo. It is 5.6km long and climbs up the hillside overlooking the Mediterranean and through the olive trees at an average of 4.1%. There are hairpins and straighter sections, where wind direction is also vital. A headwind makes attacks far more difficult.

If UAE set a fast, nine-minute tempo on the Cipressa and then Pogačar attacks near the summit, would anyone dare go with him?

Tom Pidcock could be tempted.

"That's a good question…." he told Cyclingnews.

"It all depends. If he goes by himself, I'm not sure it's the right tactic to go with him. But if anyone else goes with Pogačar, then that's different.

"Who knows what will happen on the day? Things are decided in the heat of the race. It depends on the weather - if it's warm or cold, wet or dry."

If Pogačar surges away on the Cipressa, surely Mads Pedersen, Filippo Ganna, and Mathieu van der Poel would be tempted to go with him.

The top of the Cipressa is just 12.4km away from the start of the Poggio but the fast descent and main coastal road are ideal for a high-speed chase if teams have domestiques able to chase. The problem is if a Cipressa attack is stronger than the chase group.

Colombo, Sciandri, Gontchenkov and Coppolillo managed to open a 30-second gap on the Cipressa and the coast road due to a poorly organised chase by the peloton and were never seen again.

"If UAE ride the Cipressa hard then something could happen, like it did in 1996," Sciandri told Cyclingnews.

"However the weather and the wind is the key. People watching at home can't feel the wind out on the road but it is a vital factor in races. An attack on the Cipressa into a headwind is pointless because it'll also be a headwind on the flat road to the Cipressa. Anyone with a teammate can just sit on the wheel and catch the attackers.

"If a small group goes clear and the conditions are right, then they have to all be 100% committed, and that is another problem that can turn a Cipressa attack into a waste of energy and so a big mistake.

Attacking on the Cipressa would be a big gamble for Pogačar, he'd go all-in without knowing his odds and if the attack would work. It's risky. He can't use up his team on the Cipressa like he did in 2024 because he needs them for the Poggio when it's almost certain that the really decisive attacks will be made."

Caleb Ewan's alternative strategy advice

Caleb Ewan was perhaps never considered a Milan-San Remo contender and will not ride this year after his off-season move to Ineos Grenadiers. However, the Australian sprinter won the 18-rider sprint for second place in 2018 when Vincenzo Nibali attacked alone off the Poggio descent. He was also second in 2021 when Jasper Stuyven pulled off a similar move.

As a sprinter, Ewan knows the art of survival better than most, it helps him stay in the peloton before he uses his fast finish. Ewan is aware of Pogačar's Milan-San Remo's chances but also his weaknesses. He advised him to do a radically different tactic and focus on one big attack on the Poggio.

"I think he'll win it one day but it's going to be hard for him, just because of the in-between guys like Van der Poel, who can climb and sprint," Ewan said.

"Everyone knows that he's going to try something, so everyone is ready for it and aware. The mistake that Pogačar has made before, I believe, is that he tried to make it too hard on the Cipressa, which really made the race between there and the Poggio super easy. More guys were dropped, so the leaders had fewer teammates and so the run-in to the Poggio was easier and the guys he was then trying to drop were all fresher.

"I think his best bet is to go super easy over the Cipressa, keep as many teammates as possible and then do a high-speed leadout to the Poggio and then go from the bottom, then attack them again near the top if needed."

The beauty of Milan-San Remo is that it can be decided in so many ways. A lot of riders start thinking they have a chance of victory and in theory, they can.

The attacks on the Poggio can decide everything or can be swept up on the twisting descent. A rider occasionally can surge away on the flat road into San Remo but more often they are caught. Milan-San Remo can end in a sprint but then the fastest finisher can fade after 300km of fast racing or follow the wrong wheel and be boxed in along the Via Roma barriers.

Pogačar could get everything tactically right during the nearly seven hours of racing, but then he could still lose the sprint.

Sciandri rode and finished Milan-San Remo 12 times during his career. He was third in 1993, fourth in 1997 and then crashed over the finish line in 1997 after a touch of wheels as Erik Zabel won the sprint.

"Pogačar could win even this year, but he could also lose time and time again like me. That's the magic of Milan-San Remo" Sciandri concluded.