Britain’s Cameron Norrie, Jack Draper and Dan Evans are all through to the third round of the Canadian Open, as Nick Kyrgios came from a set down to beat world number one Daniil Medvedev.
Draper, 20, defeated Greek Stefanos Tsitsipas 7-5 7-6 (7-4) to claim his first victory over a top 10 player.
Evans beat world number eight Andrey Rublev 6-4 6-4 in Montreal.
British number one Norrie, 26, came through 6-1 6-2 against Dutchman Botic van de Zandschulp.
Wimbledon finalist Kyrgios, 27, lost a first-set tie-break but the Australian fought back to win 6-7 (1-7) 6-4 6-2.
The Australian, who ended a three-year ATP Tour title drought last week at the Citi Open in Washington without losing a set, dismissed suggestions the victory against Medvedev should mark some sort of career high.
“You guys are acting like I haven’t beaten world number ones before or something,” he told reporters.
“I’ve done it before. I’ve beaten Medvedev before. I’ve beaten Roger [Federer], Novak [Djokovic], Rafa [Nadal].
“I didn’t go out there thinking that he was world number one. We played each other three times. He’s beaten me once, I’ve beaten him twice.”
Also on Wednesday, 22-time Grand Slam champion Rafael Nadal confirmed that he will compete at next week’s Cincinnati Open, having missed the Canadian Open because of the abdominal injury he suffered at Wimbledon.
World number 82 Draper had to fight back from a break down in the second set before sealing the win against Tsitsipas – who made 40 unforced errors – just before 1am in Montreal.
He will face 17th seed Gael Monfils of France for a place in the quarter-finals on Thursday, while 32-year-old Evans takes on American Taylor Fritz.
After his win, Draper said: “This is why I put in all the hard work, for nights like this on stages like this.
“Last week, me and my coach probably were thinking we weren’t even going to come here. We were going to maybe train a week, get a bit of confidence. But it paid off coming.
“He’s at the top of the game for a reason, someone I’ve looked up to the last few years. It’s just good to be out here and try to express myself on this stage.”
Norrie, meanwhile, will play Felix Auger-Aliassime for the second time in a week after he beat the Canadian on Saturday in the Los Cabos Open semi-final for the first time in five meetings.
Kyrgios continues fine form
Kyrgios recorded his eighth successive victory – but only his second against a reigning world number one – as he continued his excellent form.
The world number 37, who does not have a coach, reached his first Grand Slam final at Wimbledon in July, losing to top seed Novak Djokovic in four sets.
Even though Kyrgios has won 14 of his past 15 matches, the lack of ranking points at Wimbledon and his position in the standings meant he was unseeded for the tournament in Canada.
Medvedev, who had a bye in the first round, said it was “unfortunate” to meet a player of Kyrgios’ calibre in the opening stages.
He added: “The only thing that was a shame for me is that I played him so early because he is fit. He is among the top 10 or 15 players, so he will soon be a seeded player. It’s a shame to have such a player as an opponent in the first round.”
Kyrgios will meet Alex de Minaur for a place in the quarter-finals, after his compatriot beat Bulgarian 15th seed Grigor Dimitrov 7-6 (7-4) 7-5.
Spanish second seed Carlos Alcaraz missed a match point as he was beaten 6-7 (4-7) 7-6 (9-7) 6-3 by American world number 34 Tommy Paul, who set up a match against Croat Marin Cilic.
Norwegian fourth seed Casper Ruud overcame Slovak Alex Molcan 7-6 (7-3) 6-3 and will play Spaniard Roberto Bautista Agut, while Italy’s seventh seed Jannik Sinner, who beat Frenchman Adrian Mannarino 2-6 6-4 6-2, faces Pablo Carreno Busta.
