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Rafael Nadal may have won the Rogers Cup three times, but it’s a recent upset loss that sticks in his mind the most.

Nadal won in 2005, 2008 and most recently in 2013, where he beat Canada’s Milos Raonic 6-2, 6-2 in Montreal. However, his strongest memory of playing in Canada was last year’s third round when he was upset by Denis Shapovalov, a wild-card entry in Montreal.

“It was a great feeling, playing Shapovalov. Not at the end,” said Nadal, who lost in three sets, with a laugh. “It was a tough loss for me in that moment because it was a chance to become a world No. 1 again. Losing that match, I missed out on that chance.”

Shapovalov, who enters this year’s tournament as the top-ranked Canadian in the draw at No. 26 in the world, went on to lose to Germany’s Alexander Zverev in the semi-final. Zverev is the second seed this year.

Shapovalov, from Richmond Hill, Ont., will face France’s Jérémy Chardy in the tournament’s first round. On the other side of the bracket, Raonic, from Thornhill, Ont., will take on 10th seed David Goffin of Belgium.

Vancouver’s Vasek Pospisil is in the same bracket as Shapovalov and will face Croatia’s Borna Coric. Peter Polansky of Thornhill will play Australia’s Matthew Ebden, and promising teenager Félix Auger-Aliassime of Montreal takes on 19th seed Lucas Pouille of France.

A rematch of the Wimbledon final is already on the horizon for the women in Montreal. American Serena Williams could face Angelique Kerber of Germany as early as the second round following the women’s draw on Friday.

Friday’s draw was particularly good for the Canadians in the tournament, including Montreal’s Eugenie Bouchard (ranked No. 123 in the world).

The Westmount, Que., native avoided a top-10 player for at least the first two rounds.

She faces 15th-ranked Elise Mertens of Belgium in the first round, which will likely take place Monday at IGA Stadium. Bouchard would face either Shuai Zhang of China (No. 32) or a qualifier in the second round.

Bouchard’s half of the table does not have Serena or Venus Williams, Kerber, Maria Sharapova or world No. 1 Simona Halep.