Chris O'Connell, Alex de Minaur and Aleksandar Vukic have joined Alexei Popyrin in the third round of the Canadian Masters after recording victories in Toronto on Thursday (AEST).
O'Connell set up an all-Australian showdown with De Minaur after he denied former world No.3 Stefanos Tsitsipas 6-4 4-6 6-2, while Vukic held off a late fightback to claim victory 6-3 6-7(2) 6-3 against British No.2 Cameron Norrie for his second third-round appearance in Canada.
After Tsitsipas levelled proceedings in the second set, O'Connell dominated in the deciding set to stay alive in Toronto.
The 31-year-old progresses to the final 32 at a Masters 1000 event for the second time, having previously reached the milestone in Miami in 2024.
De Minaur awaits his compatriot after he continued his North American winning streak. The recently crowned Washington Open champion cruised to a straight-sets win over Argentinian Francisco Comesana, his sixth-straight triumph.
The world No.8 was dominant at the net, earning 10 net points to Comesana's one in the 6-4 6-2 win. De Minaur aims to go one step further in Toronto than his most recent trip there two years ago when he was a finalist.
Earlier on Thursday, Vukic upset Norrie to book his spot in the final 32. The 29-year-old won 21 points on Norrie's second serve in the three-set battle, 11 more than Norrie registered.
The world No.99 matched his deepest run there from 2023. A lucky loser at that event, Vukic beat Borna Coric and Sebastian Korda to reach that stage for the first time at a Masters 1000 tournament.
> MORE: Popyrin to defend Masters crown in Toronto
Vukic, who returned to the top 100 this week, wrapped up the first set in 33 minutes after Norrie, the world No.39, saved four break points but still dropped his opening service game.
That proved to be the only break of serve across the opening two sets as Norrie, the Wimbledon 2025 quarterfinalist, levelled the match in a tiebreak.
Vukic survived two break points in the fifth game of the final set, a moment that proved pivotal after Norrie consequently failed to hold. The New South Welshman was one game from victory when a rain delay hit before he returned to finish the job.
He next faces No.7 seed Frances Tiafoe.
In Montreal, McCartney Kessler proved too good for Maya Joint at the WTA 1000 event as she rallied from a set down to defeat the Australian teenager. Joint now turns her attention to the Cincinnati Open, which begins on 7 August.
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