The Monuments: the biggest, longest, toughest one-day races in cycling. No one wins the first Monument classic they ride, they are races that require experience, cunning, and the sort of seasoning that a few years at the front of the bunch brings the legs. 

And very few thought Mark Cavendish would win his first monument in 2009, when he took on Milan - Sanremo.

Too steep on the Poggio, too much for the fast man from the Isle of Man. Whisper it, but the word was he had too much puppy fat, and the naivety of youth that would count against him in a race that rewards patience and timing.

But on 21 March 2009, Mark Cavendish tore up the Milan–San Remo script.

Pre-race, Cav was the hottest of topics. He'd already established himself as the fastest of the fast men, bagging four stages at the 2008 Tour, but a Monument was a different matter. The 298km Classic might end in a sprint, but the warp-speed dash up the Poggio was where flat-loving sprinters went to die, and everyone knew Cavendish struggled on even the smallest of hills. Cav was hot property, sure, but this was his first tilt at La Classicissima. Even his own team wondered if he’d cling on.

The race unfolded, the long wait and rising speeds, the bunch stringing out over the Capi. The Cipressa whittled the group. Cavendish still there, at the back, suffering. 

The Poggio, and the inevitable attacks as the mountain goats looked to drop the cheetahs. Clinging on by fingertips to the tail of the leaders as the Ligurian coast came into view. The descent - still there, reduced bunch, moving forwards, sprint royale looming.

Cavendish had survived – which meant he was the man to beat. But then, with the finish in sight, Heinrich Haussler lit it up. Like a cork from a bottle he exploded from the bunch, instantly creating the gap, out the saddle with an erect style, maximum commitment. The perfect move, and the bunch watched Cavendish, and waited. Haussler looked home and hosed.

Cavendish was faced with the choice no sprinter wants: wait and lose, or go now – from way too far out. He went. We've watched thousands of sprints in our time, but I don't think I've ever seen acceleration quite like it.

The metres ticked away, the finish line closing, Cavendish getting closer, closer. The contrast in style was immense, Haussler upright, Cavendish compact, visibly faster, but still surely the line would come too soon for the catch.

Bike throw. Victory – by millimetres. Watching, we couldn't call it - but Cavendish knew, with that sprinter's sixth sense and timing. Agony for Haussler, so close to the biggest day of his career... but sometimes you just can't argue with true greatness.

Every Top Ten tells a story, and this one tells you the day that a good sprinter became one of the true greats.

It was Britain’s first Monument win since Tom Simpson, and - for our money - the greatest sprint of all time, and a worthy candidate for our second, limited edition Top Ten t-shirt.

San Remo ’09 joins our Top Ten Tees collection – celebrating the moments that make cycling legend. A British Monument victory after 42 years and a bold, beautiful addition to your wardrobe.

The Details

• Top Ten Tees: San Remo '09
• Available now - for ten days only - last day 05.09.25
• Delivery begins 7 days after the window opens

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