In the early years the main difficulty was the Passo del Turchino, but when cycling became more professional the climb was too far from the finish to be decisive.
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The 1907 Milan-San Remo was the 1st edition of the Milan – San Remo, a classic one-day cycle race organised by La Gazzetta dello Sport in Italy.
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After being approached by the Unione Sportiva Sanremese with idea of finishing a cycle race in San Remo, Costamagna decided on Milan as a starting point, connecting the hub of the Italian cycling industry with the hub of tourism.
The 1982 Milan-San Remo was won by relatively unknown French cyclist Marc Gomez who won after joining the early breakaway.
The 2000 Milan – San Remo was the 91st edition of the monument classic Milan – San Remo bicycle race and was won by Erik Zabel of Team Telekom.
Four times winner Erik Zabel lifted his arms to celebrate too soon and Freire won by 3 centimeters by a bike thrown at the line.
Among them, the 2008 World Champion Alessandro Ballan, the 2012 Giro d'Italia winner Ryder Hesjedal, the 2006 Milano-Sanremo winner Filippo Pozzato, and the 2008 Olympic Champion Samuel Sánchez.
Stannard put in an impressive performance in freezing conditions at the 2013 Milan – San Remo, initially riding on the front of the race in support of Geraint Thomas, then attacking with Sylvain Chavanel after Thomas crashed.