Stefanos Tsitsipas will look to extend an unbeaten run against Karen Khachanov on his 23rd birthday on Thursday after holding his nerve to reach the third round at the National Bank Open Presented by Rogers in Toronto. Since he reached his maiden ATP Masters 1000 final against Rafael Nadal in Canada in 2018, the Greek has made giants strides.

On Monday, he surpassed the Spaniard as the new No. 3 in the FedEx ATP Rankings. On Thursday, he will look to improve on an impressive record in Canada to 7-2 should he extend his ATP Head2Head ledger against Khachanov to 4-0 on Thursday.

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Tsitsipas recovered after letting five match points slip in an epic 22-minute, 28-point tie-break against Ugo Humbert, before he eventually prevailed 6-3, 6-7(13), 6-1 in his opening match. He had fallen to the Frenchman in both prior ATP Head2Head encounters, including at last month’s Tokyo Olympics.

“I didn’t want to think about it. Whatever happened happened, and I don’t want anything to affect me. I don’t want anything to get inside my head,” Tsitsipas said of missing five match point opportunities in the second set. “I just showed incredible mental balance and mental strength to overcome this difficult tie-break that I just experienced… I still had high hopes that I could pull something good off.”

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Tsitsipas remained on track for his third title of the season, following his first ATP Masters 1000 crown at the Rolex Monte-Carlo Masters and victory in Lyon. His third-round opponent, Khachanov, left the Japanese capital with a silver medal.

The Russian came up just short against Tsitsipas 7-5 in the deciding set in the Rotterdam quarter-finals in the pair’s most recent showdown in March. The 25-year-old has already scored impressive victories over in-form Briton Cameron Norrie and 15th-seeded compatriot Aslan Karatsev to reach the third round.

Top seed Daniil Medvedev continues his campaign on Thursday when he meets World No. 85 James Duckworth for a place in the quarter-finals. The Russian, a runner-up to Nadal in Montreal two years ago, survived a tricky second round against one-time doubles partner Alexander Bublik in three sets.

“I don’t know if the conditions changed with the humidity, but I was not playing well before the rain… I knew I had to play better if I was to win,” Medvedev said. “When back on the court, from the first game I felt much better. I only felt better and better during the match, he did not have one break point [after the rain]. I turned around the match completely.”

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The 29-year-old Duckworth sprung a straight-sets upset of 16th seed and Sunday’s Citi Open champion Jannik Sinner for his best result in Canada. The Australian’s previous best results at the event were three straight second-round qualifying defeats, the last of which came five years ago.

“He’s very solid off both sides. He’s got no real holes in his game. He hits with great length. That’s one of his best attributes – he’s able to put the ball so deep that it’s really hard to attack him,” Duckworth said of Medvedev. “It’s going to be tough, but I’ll go out there, give it a good crack and see what happens.”

Having joined compatriots Khachanov and Medvedev in the third round following a straight-sets victory over Fabio Fognini, fourth seed Andrey Rublev must now find a way past American John Isner to reach the quarter-finals for the first time in Canada. World No. 30 Isner won both previous ATP Head2Head meetings, including in Madrid this year, and comes off a three-set triumph over 13th seed Cristian Garin.

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