Philipsen edges razor-thin Milan-San Remo sprint
Belgian Philipsen used the bike throw manoeuvre right on the line to pip Matthews with two-time Tour de France winner Pogacar promising to come back and win next year.
The Alpecin-Deceuninck sprinter Philipsen was always the man to beat if the race came to a bunch finish, and he charged to the line with twelve other riders crossing within a second of each-other after six hours 14min 44sec of racing.
The Belgian was swift to praise his team-mate Mathieu van der Poel, who made the early sprint running for him and who will be a favourite at the upcoming Tour of Flanders and Paris-Roubaix Monuments.
"What Mathieu did in the final was incredible. I'm really proud and happy that we managed to play it out as a team," he said.
Philipsen has won six stages of the Tour de France and claimed the points jersey in last year's edition of cycling's most important Grand Tour with constant service from the prodigious Van der Poel.
"It's one of the dreams of any cyclist," said Philipsen. "Milan-San Remo may be one of the only Monuments I can win.
"I had really good legs from the start... but everything needs to fall in place. Mathieu was there and did a really big team job."
He is the first sprinter to win Milan San-Remo since Arnaud Demare's victory in 2016, while Mark Cavendish also won in 2009.
Fringe contender Britain's Tom Pidcock was in the final shake-up as were three world champions in Dane Mads Pedersen, Van der Poel and Frenchman Julian Alaphilippe.
Alaphilippe was in a position to escape but had a mechanical problem at the wrong moment as a run of bad luck continues.
"I just need to keep pushing and my luck will change," he said.
Pre-race favourites Pogacar and Van der Poel tried and failed to pull away in the final kilometres of the longest of the one-day races at over 280km.
Pogacar was again disappointed after starting the season with a crushing win at Strade Bianche earlier this month.
"I really want to win this race, I'll be back next year and I hope to do better, and I'm not talking about second," said the Slovene.
"I had incredible legs but this year was not hard enough to be a climber's race so I think I did everything I could to get third place. In this situation I couldn't do much better.
"Everything needs to be perfect (to win) and today everything wasn't perfect."
Filippo Ganna and Van der Poel were among the big hitters at the front of the peloton, with Van der Poel in his first road race of the season.
Pogacar pushed and with 6km to go broke away, with Van der Poel hot in pursuit as they crested the Poggio, but the Slovene could not build a big enough gap and Philipsen made his move with metres remaining to take a famous win.