Five things to look out for at Milan-San Remo 2021

The Big Three set for another showdown

There’s no doubt which three riders everyone will have their eyes on this weekend at Milan-San Remo. Having already gone hammer and tongs at each other during both Strade Bianche and Tirreno-Adriatico, the awesome trio of Mathieu van der Poel (Alpecin-Fenix), Wout van Aert (Jumbo-Visma) and Julian Alaphilippe (Deceuninck - Quick-Step) will once again convene to Italy to race each other, this time with the first Monument victory of the season on the line.

In the red white and blue corner, resplendent in his Dutch national champion’s jersey, is Van der Poel. He’s had the edge in the previous battles all three have been involved in, winning the Tour of Flanders last autumn and Strade Bianche earlier this month, and will be near-impossible to stop if he can produce the same watts on the Poggio as he did on the Via Santa Caterina.

In the yellow and black corner is Van Aert, who won the race last year. Although he was slightly distanced by Alaphilippe on the Poggio last year, the Belgian managed to catch up to him on the descent and beat him in a two-man sprint, and it’s that superior finishing kick — which he used to win a bunch sprint at Tirreno-Adriatico last week — that might give him an edge over the others.

Finally, in the white and rainbow-coloured corner is world champion Alaphilippe, whose attacks have been the decisive moment in each of the last two editions, leading him to win in 2019 and finish second last year. Van der Poel might have shocked him with his attack to win Strade Bianche, but after nearly 300km of racing on Saturday, on a climb Alaphilippe has mastered over the years, the Frenchman just might come out on top again.

Sam Bennett waiting in the wings for Deceuninck-QuickStep

One thing Alaphilippe has that Van der Poel and Van Aert don’t are team-mates that are also among the top favourites to claim victory, which should give either him specifically or Deceuninck - Quick-Step generally the upper-hand on Saturday.

Should Alaphilippe get away in an attack, he’ll have the luxury of being able to sit on wheels and not take a turn; and should he have an off-day, Deceuninck - Quick Step will have the option of going all out for a bunch finish, with Sam Bennett and Davide Ballerini both among the peloton’s quickest finishers.

For Bennett especially, this year’s Milan-San Remo feels like a date with destiny. From Mario Cipollini to Alessandro Petacchi to Mark Cavendish, most of the best sprinters of the past few generations have had just one Milan-San Remo when a perfect storm of form and circumstances have allowed them to take victory, and 2021 might just be that year for Bennett.

The Irishman has started the season on fire, with four World Tour wins to his name already, and is also climbing better than ever at Paris-Nice, which he’ll need to do if he’s to compete for victory at La Primavera. If he can make it over the Poggio still in the peloton, and if the race ends in a sprint, he’ll be the man to beat.

Sprinters hoping for a bunch finish

The sprinters have had a hard time of it lately at Milan-San Remo, with no edition since 2016 ending in a bunch finish, but they will nevertheless come in droves in the hope that they’ll get the chance to sprint for victory this year.

Arnaud Démare (Groupama-FDJ) was the victor last time the race ended in a sprint, and is always among the quickest at the end of a long, hard day of racing, even if he has had a slow start to the season and remains winless.

Also winless this year but with excellent records at La Primavera are Alexander Kristoff (UAE Team Emirates), who won in 2014 and has made the top ten on five other occasions, and Michael Matthews (BikeExchange), whose third-place finish last year was the second time in his career that he’s made the podium here.

On better form are Caleb Ewan (Lotto-Soudal), who was best-of-the-rest behind Vincenzo Nibali in 2018 and is up to top speed this year following a stage win at the UAE Tour; Mads Pedersen (Trek-Segafredo), who makes his Milan-San Remo debut looking to replicate his sprint win at Kuurne-Brussels-Kuurne; and Magnus Cort (EF Education-Nippo), who is a good outside bet following his stage win at Paris-Nice.

As for local favourites Elia Viviani (Cofidis) and Giacomo Nizzolo (Qhubeka-Assos), they’ll have to find some form quick if they’re to deliver a home victory, and claim a victory that every Italian sprinter longs to achieve sometime in their career.

Other contenders

While it’s widely expected that Van der Poel, Van Aert and Alaphilippe will put the hammer down on the Poggio, there are a number of other puncheurs who stand a chance of staying with

We’ve seen before — like at Gent-Wevelgem last year when Mads Pedersen was able take victory — that the big names can cancel each other out if they worry too much about each other, which could present an opportunity for someone else to slip away and sneak a win under their noses.

Michał Kwiatkowski (Ineos Grenadiers), for instance, is the kind of smart rider who could mastermind such a win, and has history here having been first over the line in 2017. Matej Mohorič (Bahrain-Victorious) also has a good record here having made the top ten in each of the last two editions, and always seems to finish long races like this with strong legs. And puncheurs like Alberto Bettiol (EF Education-Nippo), Alex Aranburu (Astana Premier Tech), Tim Wellens (Lotto-Soudal) and Søren Kragh Andersen (DSM) can all on their day produce potentially race-winning turns of pace.

Form-wise, Max Schachmann is one to watch having just won Paris-Nice, and will likely lead Bora-Hansgrohe with Peter Sagan apparently not in the shape to compete for victory. Trek-Segafredo, meanwhile, have three potential cards to play in former winner Vincenzo Nibali, Jasper Stuyven, and Quinn Simmons.

Early attacks

While attackers have been increasingly successful in recent editions, their race-winning moves have invariably been made on the Poggio, while the race’s other major climb, the Cipressa, has still been deemed as too far from the finish to be worth risking an attack on.

Might that change this year? With Van der Poel, Van Aert and Alaphilippe seemingly so much stronger than the opposition, riders who in the past have planned their strategy around attacking on the Poggio might now deduce that their only chance of winning is to try and catch them off-guard by making their moves earlier.

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Philippe Gilbert (Lotto-Soudal), for instance, is interested only in winning Milan-San Remo in order to complete the full-set of Monuments, and may therefore be really to risk everything with a daredevil attack.

And might even one of the Big Three go early too? Van der Poel in particular is partial to a long-range attack, and in current form looks as though he could win whenever he attacks. It would be unprecedented in recent times, but from what we’ve seen so far in 2021 such attacks might just be possible.