Milan-San Remo is cycling's longest Monument and one of the hardest races in the world to predict.
At 298km in 2026, it grinds riders down for the better part of seven hours before everything detonates on two short climbs near the finish.
The winner needs sprinting legs, climbing punch, and the tactical awareness to survive a full day in the saddle without burning a single match too early.
First run in 1907, it's the race Italians call La Classicissima, the Classic of Classics. And while the flat profile suggests a sprinters' affair, the last three editions tell a different story. Mathieu van der Poel's 2025 victory came from a three-man group that had blown the peloton apart on the Cipressa.
The year before that, Jasper Philipsen outsprinted what was left of a reduced bunch. Pure sprinters who can't handle a 4km climb at race pace don't win this race anymore.
This guide covers the race's history and route, explains why the Cipressa and Poggio have evolved into genuine selection tools, and breaks down the betting markets that matter for punters looking to have a crack at La Primavera.
What Is Milan-San Remo?
Milan-San Remo has been running since 1907, making it one of cycling's five Monuments alongside the Tour of Flanders, Paris-Roubaix, Liege-Bastogne-Liege, and the Giro di Lombardia. It's the first Monument on the calendar each year, landing in mid-March when the European peloton is still shaking off the winter cobwebs.
The Italians gave it the nickname La Classicissima because they consider it the pinnacle of one-day racing. That's a bold claim given the cobblestones of Roubaix and the brutality of Flanders, but Milan-San Remo earns it through sheer scale. No other one-day race asks riders to cover nearly 300km. The attrition is invisible for most of the day, then savage in the final 25km.
Eddy Merckx holds the all-time record with seven victories, a number that speaks to how dominant you need to be across multiple disciplines to win repeatedly. Costante Girardengo managed six wins and 11 podium finishes between 1918 and 1928. More recently, the roll call includes Erik Zabel, Oscar Freire, Mark Cavendish, Fabian Cancellara, and Vincenzo Nibali. Sprinters, rouleurs, classics specialists, climbers. They've all won this race.
That variety is the point. Milan-San Remo doesn't belong to one type of rider. It belongs to whoever reads the race best on the day.
The Route, Climbs, and Why 298km Matters
The 2026 edition starts from Pavia, south of Milan, adding roughly 10km to the opening phase compared to recent years. That pushes the total distance to 298km, the longest edition in five years. Those extra kilometres might seem trivial on paper. They're not. Every additional kilometre in the opening hours deepens the fatigue that hits on the climbs, and deeper fatigue means fewer riders capable of responding when the accelerations come.
The first 200km roll through the Lombardy plains and over the Passo del Turchino before the race drops to the Ligurian coast. It's largely processional, controlled by the sprinters' teams who want to keep everything together. The three coastal capes, Capo Mele, Capo Cervo, and Capo Berta, add undulation and the first real sting in the legs, but they rarely produce decisive action.
Then comes the Cipressa.
The Cipressa is 5.6km at an average of 4.1%, topping out with 21.5km still to race. It's not steep enough to shatter the peloton on its own, but it's steep enough to thin it. Attacks here are becoming more common, and in 2025, Tadej Pogacar lit the fuse on the Cipressa and reduced the front group to just three riders. That early aggression set up the entire finale.
The Poggio di Sanremo is the race's centrepiece. Starting 9km from the finish, it's only 4km long at 3.7% average, but the maximum gradient hits 8% near the summit. Riders crest the top with 5.4km remaining, all of it downhill on a technical, twisting descent into San Remo. The gap between summit and finish line is what makes the Poggio so compelling for punters. Attack at the top and you still need to descend like a maniac and hold off the chasers on the flat run to Via Roma.
Total elevation gain across the entire route sits around 2,000 metres. For context, that's still less than a medium mountain stage in the Tour de France. The difficulty isn't in the climbing itself. It's the climbing after 270km of racing.
Who Wins Milan-San Remo?
The old answer was sprinters. For decades, Milan-San Remo was the one Monument where a fast man could realistically target victory, and names like Zabel, Freire, and Cavendish reinforced that narrative.
That template has been ripped up. Van der Poel's 2023 win came from a solo attack on the Poggio descent; his 2025 victory was settled by a three-man group sprint on Via Roma after Pogacar's Cipressa fireworks reduced the front bunch.
Philipsen's 2024 win did come from a sprint, but it was a reduced bunch that had been carved up by attacks. Pogacar has finished on the podium twice by going on the offensive over the Cipressa and Poggio, and the only reason he hasn't won is that van der Poel keeps beating him.
The modern Milan-San Remo winner needs three things: the endurance to handle 298km without fading, the power-to-weight ratio to survive accelerations on 4% gradients after six hours of racing, and either enough sprint speed to finish it off or the descending skills to go solo off the Poggio.
Pure sprinters are now the outsiders. A rider like Caleb Ewan, who would've been a genuine contender a decade ago, simply can't hold the wheel on the Cipressa when Pogacar or van der Poel decide to push the pace. The race has shifted toward versatile riders, the all-rounders and classics specialists who combine endurance, climbing ability, and a fast finish.
2026 Contenders and Form
Two riders tower above the rest in the 2026 market, and then there's everyone else.
Mathieu van der Poel
The defending champion and two-time winner. Van der Poel's strength in this race is his ability to handle whatever gets thrown at him. When Pogacar attacked the Cipressa in 2025, van der Poel was one of two riders who stayed with him. When it came to the sprint on Via Roma, nobody could match his acceleration. He's won eight Monument titles and thrives on ultra-distance efforts where attrition favours preparation and bike handling over pure pace. The longer 2026 route plays into his hands.
Tadej Pogacar
Pogacar has finished on the podium in two of the last three editions and made the race in both. His strategy is consistent: attack on the climbs and try to drop everyone before the sprint. It hasn't worked yet because van der Poel matches him every time, but the margins are tiny. In 2025, only two riders could follow his Cipressa acceleration. The extra distance in 2026 might soften the legs of his rivals just enough for his climbing aggression to stick. Or van der Poel might simply follow him again. That duel is the race.
Jasper Philipsen
The 2024 winner proved he can handle the climbs well enough to stay in contention when the pace lifts. Philipsen isn't going to attack on the Poggio, but if the group comes back together, he's got the fastest finish of anyone in the race. His chances depend heavily on whether the climbers' attacks succeed or fail. If a group of eight or more hits Via Roma together, Philipsen is the man to beat.
Filippo Ganna
Ganna's emergence as a Milan-San Remo contender surprised a lot of people in 2025, but the big Italian time triallist has reinvented himself as a classics rider. Second place behind van der Poel confirmed he can hang with the best on the climbs, and his raw power on the flat sections means he's nearly impossible to drop once the road levels out. A genuine threat if the race comes down to a small group sprint.
The Next Tier
Tom Pidcock brings climbing pedigree and cyclocross handling skills that translate perfectly to the Poggio descent. Michael Matthews has the sprint speed and the experience, finishing on the podium in 2024. Matej Mohoric won the race in 2022 with a daring solo attack on the Poggio descent and can't be discounted. Wout van Aert, if fit and in form, is capable of winning any one-day race on the calendar. Julian Alaphilippe has the punch for the Poggio but has struggled with consistency in recent seasons.
Betting Markets (and How to Approach Them)
Milan-San Remo offers a handful of distinct markets, each with different risk-reward profiles for punters.
Outright Winner
The headline market. Van der Poel and Pogacar are short-priced co-favourites, and that pricing reflects reality. These two have dominated the race for three consecutive editions. Beyond them, Philipsen and Ganna offer value as riders who've proven they belong at the pointy end. Further down the market, riders like Pidcock and Mohoric are longer shots with legitimate winning credentials.
Head-to-Head Matchups
These markets pit two riders against each other, and you're simply picking which one finishes higher. Key pairings to watch include van der Poel vs Pogacar, which is essentially a bet on whether climbing aggression or sprint superiority decides the race. Van der Poel vs Philipsen comes down to whether the race stays together or splinters on the climbs. Pogacar vs Ganna is another interesting matchup, with Pogacar's attacking style versus Ganna's diesel engine on the flat.
Place Betting
Top 3 or top 5 markets reduce the risk compared to outright picks. A place bet on Ganna or Pidcock offers decent value given their ability to stay in contention without necessarily winning. This market also suits punters who fancy a longer-priced classics specialist like Mohoric or Matthews to ride into the top five without needing everything to fall their way.
Nationality and Team Props
If available, these markets let you back a country or team rather than an individual. The Netherlands (van der Poel), Slovenia (Pogacar), and Belgium (Philipsen) are the obvious picks, but Italy (Ganna) offers an interesting angle given the home crowd factor and Ganna's rising trajectory in this race.
How to Watch Milan-San Remo in Australia
SBS holds the broadcast rights for Milan-San Remo in Australia, and the race is available free-to-air and on SBS On Demand. The 2026 men's race starts at approximately 8:00pm AEDT on Saturday 21 March, with the finish expected around 3:00am AEDT early Sunday morning. It's a late night if you want to watch the whole thing, but the Cipressa and Poggio action kicks off in the final 90 minutes, so tuning in from around 1:30am gets you the business end.
SBS typically broadcasts the women's race earlier in the day. Check SBS Sport's schedule closer to race day for confirmed timings.
Milan-San Remo FAQ
What makes Milan-San Remo different from other Monuments?
Distance. At 298km in 2026, it's comfortably the longest one-day race on the professional calendar. Where Paris-Roubaix tests riders with cobblestones and the Tour of Flanders throws wall after wall at them, Milan-San Remo grinds through nearly 300km of relatively flat terrain before concentrating the difficulty into two short, sharp climbs near the finish. The race rewards patience and endurance as much as explosive power.
Why is Milan-San Remo the longest one-day race?
Tradition, mostly. The race has connected Milan to San Remo since 1907, and the geography between those two cities demands a long route. Organisers have tweaked the starting point over the years, but the commitment to covering the full distance between Lombardy and the Ligurian coast has kept it well above 280km for over a century. The 2026 edition starts from Pavia rather than central Milan, adding an extra 10km to the opening phase.
Has the race gotten harder in recent years?
The route itself hasn't changed dramatically, but the racing has. The current generation of riders, led by Pogacar and van der Poel, attack earlier and harder than their predecessors. The Cipressa, which used to be a warm-up for the Poggio, is now a genuine selection point. Three of the last four editions have been decided by solo attacks or small groups rather than bunch sprints, which represents a real shift from the race's historical pattern.
Are there intermediate sprints or time checks to bet on?
Milan-San Remo doesn't feature significant intermediate sprints in the way a stage race does. The race structure is essentially one long build-up to the Cipressa and Poggio, with no meaningful intermediate competitions. Betting markets focus on the final result: outright winner, place finishes, and head-to-head matchups. For punters interested in cycling outright markets, Milan-San Remo represents one of the season's marquee one-day betting opportunities.
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