The Thornhill, Ont., native won by scores of 7-5, 7-6 (5) over the Russian despite having some trouble getting his first serve into play.
Up next is Fernando Verdasco, who in 2011 had critical words for Raonic after losing twice to him on hardcourts.
"I hope to play soon against him in clay court to show him what it is to play tennis, and play rallies, and run, and not [just] serve," said Verdasco.
The Spaniard beat Raonic in two subsequent matches on clay, and 10 of his 17 career ATP finals have come on the surface.
Other winners Monday included No. 12 Kei Nishikori of Japan, Germany's Florian Mayers, Denis Istomin of Uzbekistan, and Kevin Anderson of South Africa.