To get from Monaco to Sanremo, Michael Matthews has plotted his own route down a bike path which means he can cross the border from France to Italy without having to ride on traffic-heavy roads. Over the winter, he has ridden the finale of La Classicissima, the longest bike race on the WorldTour calendar, an estimated 30 times. Up and over the Cipressa, then the Poggio, then the technical descent, then the run into the finish line. It’s become muscle memory for the Australian rider.
There’s a famous quote by Albert Einstein: "The definition of insanity is doing the same thing over and over again and expecting different results.” With six top-ten finishes and three podiums in eleven participations, Milan-Sanremo is on the verge of slowly driving Michael Matthews to insanity. He says he has watched the finale of last year’s race “multiple times” analysing the moment his sunglasses started to slide off his face during the sprint, and wondering if that split second, or that momentary lapse of concentration, was what meant Jasper Philipsen edged his front wheel in front of the 34-year-old at the finish line.
“It was honestly very difficult to swallow that result, knowing that with 25 meters to go, I was still in front and about to win my first Monument,” Matthews says. “I've had to work a lot to get back to try and fight for it again this year. It hasn't been an easy process. I don't think it's ever happened in cycling that someone lost a Monument because their glasses fell off. Let's not repeat that.”

Image: Zac Williams/SWpix.com
Part of the fuel behind Matthews’ obsession and addiction to Milan-Sanremo is how close he’s come so many times to everything working out. Every top-10 finish, every time he stands on the podium, it feels like next year could be the year that the stars align. There’s always another chance.
“Maybe I need to try something different, but that's where you have to assess at the moment whether you have the legs to attack or to wait for the sprint. There's really a million scenarios going through your head of what you should actually do, where you should use your energy, which wheels you should follow, who else is in the bunch, what's happened through the race,” Matthew says.
“It's like no other race, because you're so tired, you're so fatigued, it's been such a long day on the bike. It's all about making the right decision at that right moment. Unfortunately, I haven’t been able to make the right decision yet. But hopefully this year.”
Like the sport of cycling as a whole, Milan-Sanremo is a race that’s always evolving, which is why it’s so tricky to find the winning formula. That final duo of climbs with the Cipressa and the Poggio are the same, but the changing dynamics of the modern peloton has meant different riders are in contention to win. Since Matthews’ first participation in 2011 – coincidentally when the race was won by fellow Aussie Matthew Goss in HTC-High Road colours – he says it’s harder to take victory than ever, because it’s not just puncheurs or sprinters you have to be aware of.
“It's changed massively. When I was first riding it, it was known as the sprint race. Basically, all the sprinters would get over the climb and it would be a big bunch kick. Then obviously more climbers saw that making it hard was possible. It can change depending on the characteristics of the favourite to win the race and if they have the strongest team to make the race the way they want it,” Matthews states.

Image: Jayco-Alula
14 years on from his first taste of Sanremo, Matthews starts the 2025 edition as one of the contenders, but he’s not the stand-out favourite to win. It’s the world champion Tadej Pogačar who takes that title, especially after his performance at Strade Bianche just one week ago. Both residing on the French Rivera, the UAE Team Emirates-XRG rider is a close friend of Matthews, with Pogačar even giving his Aussie competitor a lift to the start of Sanremo last season. After the Slovenian rider’s third place finish in La Classicissima last year, Matthews knows that Pogačar has the potential to win the race, but says that it’s not going to be easy for him to get rid of the fast men.
“Every race Tadej goes to he's normally the biggest favourite, but this is probably one of the hardest races for him to win. It's not as selective early on as he would like personally. It's up to his team to make it as hard as possible for the rest of us to get to the finish,” Matthews comments.
How exactly do they do that? “It's been tried multiple different ways in the past, but I think they just need to go as hard as possible, as early as possible, and just keep going. They showed in Strade Bianche for the last two years they can make it hard early and get a small bunch. That doesn’t really suit the Sanremo course – but they don’t have much other choice.”
And what is it like to have one of your closest friends as one of your closest rivals in the race that means most to you? Matthews admits that it’s a strange dynamic, but a positive one.
“On the bike we talk during the race, but when it comes down to the finals there is no love lost. We need to race each other. There's no helping each other or anything. We can turn our brains off and just and just race for our teams and race for ourselves which is our job,” Matthews says pragmatically.
The Jayco-Alula rider has given too much to this bike race for too long to let anything get in the way of a potential Milan-Sanremo victory. In the pursuit of a Monument win, friendships are secondary – the top step of the podium in Italy on Saturday is what matters. Whether he’s the pre-race favourite, or an outside bet for victory, Matthews says he doesn’t care. This is Milan-Sanremo, the race that has his heart, with the finale he has spent the winter months studying over and over again. It’s the same question he’s asked – we all ask – every season he has taken to the start line in Pavia: Could this be the year that Bling finally does it?
Cover image: Zac Williams/SWpix.com