Pogacar's biggest conundrum: Breaking down his five tilts at Milan-Sanremo

Milan-Sanremo is a race like no other. If cycling were invented from scratch today, nobody would think to make an interminably long and largely flat race from Milan to the Riviera one of the biggest events on the calendar. But that anachronistic feel is a large part of Milan-Sanremo’s charm, and it feels more essential than ever in the 2020s.

These days, the strongest riders win the biggest races with clockwork regularity. Tadej Pogačar, in particular, routinely divests the sport’s landmark events of any semblance of suspense with his overwhelming strength. 

But some races remain just beyond his grasp. He’ll take a second tilt at Paris-Roubaix later this spring, of course, but he has already had repeated attempts at Milan-Sanremo and he has not yet found a way to unlock the subtleties of the race.

Pogačar being Pogačar, he has still changed the complexion of the race. The Milan-Sanremo of today feels radically different to a generation ago. The few sprinters who make the trip these days line up in hope rather than expectation, while the Cipressa is now a viable springboard for the winning move.

But Milan-Sanremo remains the thinking rider’s Monument, a race where finesse matters just as much as force. Unlike Mathieu van der Poel, Pogačar hasn’t yet found the right balance, but there are lessons to be drawn from his five previous attempts ahead of Saturday’s showdown on the Riviera.

Winner: Wout van Aert

Pogačar’s position: 12th at two seconds

Pogačar’s first attack: N/A

The summer of 2020 was a different time, and Tadej Pogačar was still hiding in plain sight. True, he had placed on the podium of the previous year’s Vuelta a España, but Remco Evenepoel’s dazzling feats of strength meant that the Slovenian wasn’t even the most acclaimed emerging talent in the sport at this point.

That would all change at the following month’s Tour de France, but Pogačar was a relatively low-key presence at his debut Milan-Sanremo, which took place in early August of this pandemic-condensed season. For context, 2014 winner Alexander Kristoff and Fernando Gaviria were UAE Team Emirates’ leaders for the race.

The shift in date had also triggered a change in the route after towns along the Ligurian coast opposed the race’s passage at the height of tourist season. In any case, RCS Sport’s new route via the Langhe was a worthy substitute, and the high-octane finale remained intact. 

Pogačar was in the reduced peloton that hit the foot of the Poggio together, but he would make no impression on the climb, where Julian Alaphilippe and Wout van Aert simply had too much power for everybody else. Van Aert scrambled back up to Alaphilippe on the descent and then outsprinted him on the Via Roma to claim his first Monument. It looked like the first of many.

The so-called ‘new cycling’ had probably already started a year or so previously, but this edition of Milan-Sanremo was a clear sign of things to come in the 2020s. When Vincenzo Nibali escaped on the Poggio to win in 2018, he had benefited from tactical inertia behind, where everybody was waiting for Peter Sagan to respond and the Slovakian, tired of the man marking, called their bluff. 

By 2020, such hesitance already seemed to belong to a different era. Nobody was standing on ceremony when Alaphilippe and Van Aert accelerated, but their raw power was too much to handle. Pogačar, who briefly led the chase on the descent before coming home in 12th place, clearly took note.

Winner: Matej Mohorič

Pogačar’s position: Fifth at two seconds

Pogačar’s first attack: 8.5km to go

By the time Pogačar returned to Milan-Sanremo in 2022, he was a two-time Tour de France champion and a double Monument winner. Perhaps more pertinently, he had just won Strade Bianche with a stunning 50km solo raid. Pogačar has made those long-range efforts seem routine in recent years, but four years ago, this was all bewilderingly new, and his very presence made this the most eagerly anticipated edition of Milan-Sanremo in a generation.

UAE’s forcing on the Cipressa cut the bunch to just 30 riders, and as they sped towards the foot of the Poggio, the men in the front group were already bracing themselves for impact.

After a lead-out from Diego Ulissi, Pogačar launched his first acceleration with almost 3km of the Poggio still to race. When Van Aert resisted, Pogačar simply kept on going. Conventional wisdom suggested a rider had one shot at attacking on the Poggio and he had to use his bullet wisely, but that thinking seemingly no longer applied. Pogačar launched four attacks and made huge accelerations to respond to two more on the way up the climb, an onslaught that brought to mind Giorgio Furlan in 1994.

Unlike the Gewiss man, however, Pogačar had company at the summit in the form of Søren Kragh Andersen, Van Aert and Mathieu van der Poel. They would be overhauled on the descent, by Pogačar’s compatriot Matej Mohoric. Equipped with a dropper post, Mohoric took risks nobody else was willing to countenance, and it was Pogačar himself who left the decisive gap open. 

A frustrated Pogačar came home in fifth place, and he confessed afterwards that he had made a tactical error, attacking a hairpin earlier than he had been instructed. “I attacked too early and into a headwind the first time on the Poggio,” Pogačar said. “That’s a mistake you can’t repair at Milan-Sanremo.” 

Winner: Mathieu van der Poel

Pogačar’s position: Fourth at 15 seconds

Pogačar’s first attack: 6.6km to go

The previous year may have been a lesson in the subtleties of Milan-Sanremo, but that didn’t mean Pogačar and UAE weren’t going to reach for the sledgehammer again when they returned in 2023. 

There were persistent mutterings in the build-up that Pogačar would seek to ignite the race on the Cipressa, but that storm never quite materialised. UAE set a bracing pace, but it served to whittle down the peloton rather than blow it apart, and Van der Poel led over the summit, while Bahrain Victorious were in command as the race hit the base of the Poggio.

UAE sprang into action 2.5km from the top, when Tim Wellens launched a rasping acceleration with Pogačar on his wheel. Their speed was such that they were braking into the corners, but the elastic was just about holding behind.

Pogačar’s own attack eventually came when Wellens swung off just over a kilometre from the top. He opened a small gap by burning Kragh Andersen off his wheel, but he couldn’t get full separation. First Filippo Ganna latched back on and then Van Aert dragged Van der Poel with him to make a leading quartet on the final ramp before the summit.

Although Pogačar had been more patient than in 2023, he still did too much too soon here. Van der Poel, by contrast, delivered a masterclass in choosing your moment at Milan-Sanremo, accelerating with intent just as the leaders were preparing themselves to crest the Poggio. By the time Pogačar realised what had happened, Van der Poel already had 20 metres. Game over.

The longest Classic is so often decided by split-second decisions, and Van der Poel’s timing was impeccable. He won on the Via Roma, while Ganna and Van Aert squeezed Pogačar off the podium – and the infamously cramped couch.

“Maybe I was just not strong enough to go solo to the top,” Pogačar said afterwards, though deep down, he surely knew he had been given a lesson in the strategy of winning this maddeningly beguiling race. “Mathieu was sprinting at the top of the Poggio, and I was already dead from my turn.” 

Winner: Jasper Philipsen

Pogačar’s position: Third at same time

Pogačar’s first attack: 6.6km to go

After a sobering second defeat to Jonas Vingegaard on the 2023 Tour, Pogačar rang the changes for the new season. Now coached by Javier Sola, Pogačar seemed to add new weapons to his armoury, and his superiority across all terrains would brook no argument over the next two seasons. And yet, Milan-Sanremo still stubbornly refused to yield to his will. 

This time out, La Primavera was only the second race on Pogačar’s schedule, but he was the obvious favourite after an 82km solo raid to win Strade Bianche in his first outing. After that showing, neither Pogačar nor UAE saw any reason to deviate too far from the previous year’s approach to Milan-Sanremo. 

The team again took up the reins on the Cipressa, but for once, they lacked the collective strength to match their strategy. With a kilometre of the climb left, Wellens was the only teammate Pogačar had left. Sagely, the offensive was called off.

Pogačar would go again on the Poggio, of course. In a near copy of 2023, Wellens provided the long lead-out before his leader accelerated a kilometre from the top of the climb. This time, it was Van der Poel himself who responded immediately, bringing Ganna and Alberto Bettiol with him before the effort petered out. 

Near the summit, Pogačar went again, almost in imitation of Van der Poel’s deft move the previous year. It would surely have paid off had Van der Poel himself not been wise to it. The world champion bounded across the gap and stitched the race back together on the descent. 

By now, Van der Poel was racing for Jasper Philipsen, and he snuffed out a late Tom Pidcock attack before his teammate scorched to sprint victory on the Via Roma. Pogačar’s positioning on the Via Roma was savvy, but he simply couldn’t match the flat-out speed of Philipsen and Michael Matthews. A first podium in Sanremo and a record time on the Poggio were scant consolation for Pogačar, who acknowledged his team had fallen short on the Cipressa.

“Everything needs to be perfection, and today not everything was perfect,” said Pogačar, who was already clear on what to remedy for 2025. “I think actually that today was one of the easiest races ever. We rode a really, super-easy tempo the first few hours…” 

Winner: Mathieu van der Poel

Pogačar’s position: Third at same time

Pogačar’s first attack: 24.7km to go

It finally happened. Ever since his 2022 appearance, Pogačar had been teasing the idea of attacking on the Cipressa. After running up against Van der Poel’s mastery of the Poggio the previous two years, Pogačar and UAE Team Emirates-XRG went for broke in 2025.

Tim Wellens was now deployed early on the Cipressa before new signing Jhonathan Narváez – not for the last time in 2025 – conjured up a supersonic lead-out for Pogačar. Exactly 3km from the top of the Poggio, and with 24.7km still to race, Pogačar unleashed an acceleration of astonishing fury. Not since Paolo Bettini in 2003 had a pre-race favourite attacked with such intent on the Cipressa, and even then, Il Grillo was brought back before his eventual race-winning move over the Poggio.

There was never any prospect of Pogačar being reeled in here. It was simply a question of who could hang on to the rocket. Ganna, Van der Poel and Romain Grégoire were the only men to follow the initial move, though the Frenchman was quickly jettisoned. 

Ganna, meanwhile, strained to hold firm. He was distanced 1.5km from the top, but he was able to latch back on when Pogačar realised he couldn’t break Van der Poel and the pace dropped by a percentage point. That leading trio already had a scarcely credible 40 seconds by the summit of the Cipressa.

On the Poggio, Pogačar simply repeated the dose over and again, but Van der Poel was able to absorb every blow in their slugging match. Ganna was again distanced but he cannily stuck to his pace in the hope Pogačar would eventually punch himself out.

And that’s more or less what happened. Pogačar couldn’t break Van der Poel’s resolve, and the Dutchman then struck a hefty psychological blow by launching an attack of his own within sight of the summit. Pogačar got back on terms, but the momentum of the fight was now firmly with Van der Poel.

Ganna bridged back up to them beneath the flamme rouge, but the three-way sprint had an inevitable feel about it. Even so, Pogačar made the task so much easier for Van der Poel by inexplicably backing off Ganna’s wheel in the sprint. Van der Poel cruised to victory and Pogačar couldn’t even get around Ganna for second.

“The legs were really good, but maybe I'm just missing the big power,” Pogačar said afterwards. “I could try many times but maybe it’s just that a few watts are missing.”

Perhaps, but maybe Pogačar could also look elsewhere for improvements. More than any other Classic, Milan-Sanremo is a race of wits as well as of legs. At pretty much every other event on the calendar, Pogačar’s raw strength will reliably outweigh any tactical error, but no race punishes mistakes quite like Milan-Sanremo. 

The best rider in the world tackles the biggest conundrum in cycling, and that makes it the most intriguing race of the year.