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Denis Shapovalov was victorious the first time he played fellow Canadian Milos Raonic on the ATP World Tour. The veteran will soon get a chance to avenge that loss.

The top two players in the Canadian men’s singles rankings are set to square off on Thursday at the Masters 1000 tournament in Cincinnati. Shapovalov booked his third-round ticket with a win over Britain’s Kyle Edmund on Tuesday night, while Raonic advanced on Wednesday with a 6-3, 7-5 win over Tunisian lucky loser Malek Jaziri.

“I’ve watched him for so many years representing Canada, so any chance I get to play him and take him on, it’s a privilege for me,” Shapovalov told the ATP after his win. “So I’m going to go out there and enjoy myself, kind of like I did in Madrid, and hopefully I can play as well.”

Shapovalov posted a 6-4, 6-4 victory over Raonic last May on clay in their lone head-to-head competitive meeting. The 19-year-old from Richmond Hill, Ont., won almost 80 per cent of his first-serve points, calling the win a “huge confidence boost.”

Shapovalov moved ahead of Raonic to become the Canadian No. 1 for a few months before losing the position this week.

Raonic, 27, held steady at No. 29 in the latest world rankings while Shapovalov slid six spots to No. 32 after losing the points gained from last year’s semi-final appearance at the Rogers Cup in Montreal.

The two players offer an interesting contrast in styles. Shapovalov is a flashy left-hander who can be quite demonstrative on court, while Raonic, a big-hitting right-hander, prefers a more composed approach.

Raonic, from Thornhill, Ont., has won eight career titles since turning pro a decade ago. He reached the final four at the 2016 Australian Open and made it to the Wimbledon final later that season.

“He showed the way for the next generation because Milos was [world] No. 3, in a final of a Grand Slam and in [Slam] semi-finals,” Tennis Canada vice-president of high performance Louis Borfiga said in a recent interview. “He’s had an incredible impact for the young generation.

“Milos is very, very important for the success of Canadian tennis.”

Shapovalov, who’s still looking for his first career ATP Tour win, leads a solid crop of young domestic tennis talent that includes Félix Auger-Aliassime, Françoise Abanda, Bianca Andreescu and others.

Raonic has battled a host of injuries in recent seasons but has had some good stretches this year, while Shapovalov is trying to build off his breakout rookie campaign.

Raonic struggled last week in Toronto, falling in the second round to American Frances Tiafoe. Shapovalov lost in the third round to Robin Haase of the Netherlands.

This week in Cincinnati, Shapovalov beat Tiafoe in the first round while Raonic opened with a victory over Serbian qualifier Dusan Lajovic.

The Canadians will likely be teammates next month in Davis Cup play in Toronto. Canada will face the Netherlands in a World Group playoff at Coca-Cola Coliseum.

“The future is really bright, not just for the Rogers Cup, but for Davis Cup and also for tennis in Canada,” Rogers Cup tournament director Karl Hale said. “So you’re looking at a 10-year window of tremendous and new accomplishments for tennis in Canada. So, we are very humble as Canadians, but very excited about the future.”

Play at the US$5.67-million Western & Southern Open continues through Sunday.

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