Who will be king of the spring? – How Milan-San Remo could write the next chapter of Tadej Pogačar and Mathieu van der Poel's thrilling rivalry

Milan-San Remo is the first of three rounds of the greatest prize fight in professional cycling right now. It is a battle of the titans, that is rewriting the cycling history books, fueling one of the greatest rivalries and inspiring some great racing.

Tadej Pogačar and Mathieu van der Poel will again go toe to toe, shoulder to shoulder and wheel to wheel in Italy on Saturday and then again at the Tour of Flanders and Paris-Roubaix.

Two of the sport's biggest names are facing off this spring, trying to enforce their dominance over the other in three of the sport's biggest Monument races.

Latest Videos From

They have clashed for the last three springs, first at San Remo and Flanders, and then at Roubaix last year when Pogačar made his Hell of the North debut. Van der Poel has more wins, managing to win all three of the four spring Monuments, but Pogačar is coming ever closer to beating him, something he's only done in Flanders so far. Of course, Pogačar has won Liège-Bastogne-Liège, Il Lombardia and Strade Bianche too.

The spring of 2026 could finally decide who is the king of the spring, if Pogačar really is the Merckx of his generation or if Van der Poel is one of the Classics greats of all time.

Rewriting the Monument record book

Van der Poel and Pogačar have dominated the Monuments for the last three years, swapping turns to win and lose, beating each other but dominating the biggest one-day races on the men's calendar. The two have won 13 of the last 15 Monuments, plus the last three UCI Road World Championships, leaving little on the table for their rivals.

Wout van Aert has faded away or been injured in recent seasons and Filippo Ganna is only a third incumbent at Milan-San Remo and has yet to prove his talents on the cobbles. Few others have beaten them when they are racing and at their best and the next generation has still to emerge. For now the biggest Classics are still Pogačar's and Van der Poel's world.

Pogačar's palmarès is one of the richest in cycling history and has become even more prestigious since he began chasing the spring Classics in 2022.

The Slovenian won Strade Bianche in 2022, 2024, 2025 and 2026. He travelled north to Belgium and the cobbles to prove he is far more than just a Grand Tour rider and won the Tour of Flanders in 2023 and 2025, only missing the race in 2024 to target the Giro-Tour double.

Pogačar has also ​​won Liège-Bastogne-Liège three times and now has a total of 10 Monument victories from 20 rides. Of course, only Milan-San Remo and Paris-Roubaix are missing but victory is surely only a matter of time, unless Van der Poel gets in the way again.

The Alpecin-Premier Tech leader is more of a Classics specialist but is arguably more effective on his day, with an even better strike rate than Pogačar.

He won the Tour of Flanders in 2020, 2022 and 2024 and Paris-Roubaix in 2023, 2024 and 2024. He won Milan-San Remo in 2023 and 2025 and wore the rainbow jersey in 2024 after winning in style in Glasgow. Van der Poel has won eight Monuments in 21 rides but his palmarés also include six other podium places.

Pogačar has skewed his data by his five consecutive Il Lombardia victories but there has been little room for other riders to edge their wheel over the line first when he is racing. Remco Evenepoel won Liège-Bastogne-Liège in 2023 but that was when Pogačar crashed hard and fractured his scaphoid.

Jasper Philispen won Milan-San Remo in 2024 but only thanks to the sacrifice and chasing of Van der Poel. Pogačar made a final attack near the sumit of the Poggio but they were caught and he finished 'only' fourth in the sprint.

Both Pogačar and Van der Poel are already amongst the all-time Classics winners, with years ahead of them still to race and win.

Since 2023, they have virtually swapped turns at winning, beating each other and any rare rivals in every race. In 2025, Van der Poel won Milan-San Remo, Pogačar got revenge with a solo victory at the Tour of Flanders but then Van der Poel struck again at Paris-Roubaix.

Pogačar is on the cusp of winning a fifth Tour de France and so will join Jacques Anquetil, Eddy Merckx, Bernard Hinault and Miguel Indurain in the record book of legendary Grand Tour greats.

He is chasing Monuments at the same time. Only Rik Van Looy, Eddy Merckx and Roger De Vlaeminck ever won all five Monuments but Pogačar seems within his capabilities – Van der Poel is probably his only obstacle.

Van der Poel is also the only active rider with wins in Milan-San Remo, the Tour of Flanders and Paris-Roubaix. He could even make history this year and win all three. A fourth Paris-Roubaix victory would equal Tom Boonen and Roger De Vlaeminck. Nobody has ever won four in a row but the Dutchman has a shot at that too. A third Milan-San Remo victory on Saturday could begin the pursuit of a historic spring Monument triple. Both Pogačar and Van der Poel are making history as they battle with each other.

Merckx stands atop the list of of all-time Monument victories with 19 but Pogačar can join Roger De Vlaeminck in second place with 11 Monuments if he wins Milan-San Remo. Van der Poel is moving up the list of greats with eight.

Pogačar vs Van der Poel is like Eddy Merckx vs Roger De Vlaeminck

Great rivalries are the salt of professional cycling, inspiring some of the greatest racing of all time and the best narratives.

Jonas Vingegaard has pushed Pogačar to Tour de France greatness and Van der Poel is doing the same in the Classics.

Pogačar versus Van der Poel is like a remake of Eddy Merckx versus Roger De Vlaeminck from the late sixties and early seventies. That saw the ever-aggressive Cannibal take on the more crafty De Vlaeminck, who used his fast finish and tactic skills to often outwit and so irritate Merckx.

Of course Merckx won Milan-San Remo seven times, the last exactly 50 years ago in 1976. De Vlaeminck dominated Paris-Roubaix, winning four times in 1972, 1974, 1975 and 1977. Merckx won in 1968, 1970 and 1973, as the two left few opportunities for their rivals for almost a decade.

It is unfair to directly compare generations but Merckx has modestly described Pogačar as even more prolific than he was.

"Yes, I don't see many differences. There were days when I won by a wide margin, like the 1969 Liège stage or the Tre Cime di Lavaredo stage of the 1968 Giro," he recently told La Gazzetta dello Sport.

"I see the same determination in Tadej. But let's stop there, because as you know, I don't like comparisons, especially when comparing different eras."

Merckx had simple advice for Pogačar if he wants to beat Van der Poel at this year's Milan-San Remo.

"This could be a good time for Pogačar if... he attacks at the right time. But the Van der Poel we saw at the Tirreno-Adriatico, thanks to his two stage wins and more, won't be easy to beat," Merckx warned.

"Tadej must drop him, because after 300 kilometres on Via Roma, if they were still together... the favourite would be Mathieu."

When Van der Poel won his eighth cyclocross world title, passing Erik De Vlaeminck, his brother rebuked any suggestion that the Dutchman was the greatest cyclocross rider of all time.

"Bloody hell, no. Not by a long shot," Roger told Het Nieuwsblad in early February.

Even at 78, De Vlaeminck remains as competitive as when he clashed with Merckx.

"Van der Poel, Evenepoel and Pogačar are good riders but when I watch them I can't enjoy myself. I want to race against those guys and beat them the way I sometimes beat Merckx," he said.

Changing the Cipressa racing

Pogačar and Van der Poel's battle to be the king of the Classics is so intense it has changed the nature of the racing.

Milan-San Remo was traditionally dominated by the sprinters and opportunists. Pogačar's attacks have changed the race, in the same way he has snatched the Tour of Flanders from the biggest rouleurs.

Milan-San Remo winners now need to be power climbers if they want to survive Pogačar's Cipressa and Poggio attacks. The likes of Arnaud De Lie and other sprinters are opting to stay away from Italy this spring, knowing they have little chance of victory.

Last year Pogačar produced 900 watts for a minute when he launched his first attack, the Cipressa. Van der Poel matched him and even had time to grab a bidon during a second Pogačar surge.

With Ganna hanging on for dear life, they averaged 38kph for the 5.7km Cipressa climb, setting a new record time of 8:59 according to Strava.

Pogačar's and Van der Poel's rivalry is more friendly and Gen Z than the snarkiness of Merckx and De Vlaeminck. After last year's Milan-San Remo they chatted behind the podium and then joked about going even faster this year.

"Next year Cipressa under 8 mins?" Van der Poel said provocatively under a Velon Instagram post about their power data.

Pogačar replied: "Analysing right now, we can a bit faster, like 59s"

Pogačar recently set an unofficial new best time of 8:51 in training but that was likely to be with help from a powerful scooter that was motor pacing him. We will find out if he is faster and if Van der Poel can stay with him on Saturday.

Despite a lack of the tailwind that helped Pogačar's Cipressa attack in 2025, he is expected to try to dynamite the race there, as Merckx often did as he tried to smash and grab major victories.

However Van der Poel seems ready for Pogačar's attack, as he showed at Tirreno-Adriatico. Van der Poel seems to be setting a trap for Pogačar, so that he races far too aggressively and too generously.

UAE may try to invent a different tactic this year, perhaps even upping the speed on the Turchino but they are stuck between a rock and a hard place, in a game of chess without a final checkmate move. Van der Poel holds the better cards, can follow the most effective tactic and knows it.

"Van der Poel knows exactly where Pogačar will go, on the steepest section of the Cipressa," Dutch cycling expert Thijs Zonneveld said in the In De Waaier podcast.

"Van der Poel is very capable of staying on his wheel and accelerating with him. On the Cipressa, it really comes down to raw power. He 'only' has to follow Pogačar, and then he’ll probably beat him."

Advantage Van der Poel, it seems, with the Tour of Flanders and then Paris-Roubaix the rematches of the spring.

Get unlimited access to our unrivalled 2026 Spring Classics coverage with a Cyclingnews subscription. We'll bring you breaking news, reports, and analysis from some of the biggest races on the calendar, including Milan-San Remo, Paris-Roubaix and the Tour of Flanders. Find out more.