Alexei Popyrin’s defeats 2021 champion Daniil Medvedev to reach the final 16 at the ATP Masters 1000 tournament in Toronto.

Toronto, Canada, 1 August 2025 | Jackson Mansell & AAP

Alexei Popyrin won the battle of former champions to advance to the fourth round of the ATP Masters 1000 tournament in Toronto.

Defending champ Popyrin fought back after losing the first set to beat the 2021 champion Daniil Medvedev 5-7 6-4 6-4 on Friday morning (local time) in two-and-a-half hours.

Despite the first-set deficit, Popyrin seemed in control. The Australian No.2 claimed an early break after a shaky start from the No.10 seed, who had nine unforced errors and three double faults in the first four games.

VIEW: Why Alexei Popyrin isnt looking for ‘trade-off tennis’

However, Medvedev would only cough up three more unforced errors to win the opening set in 56 minutes.

Opening-game breaks in the final two sets helped set the tone for Popyrin as the scoreboard pressure took its toll on the world No.14. Paired with his big service game and dominance at the net, the 25-year-old overcame Medvedev to extend his winning streak at the Canadian Open to eight matches.

It was a superb win for the Australian against the former world No.1 in the lead-up to the US Open later this month.

MORE: Popyrin to defend Canadian crown in Toronto

Popyrin’s victory sets up a fourth-round clash with No.5 seed Holger Rune after the Dane advanced by beating Frenchman Alexandre Muller earlier on Thursday.

The New South Welshman is one of three Australians still alive in Toronto, with Alex de Minaur joining Popyrin in the final 16 after countryman Chris O’Connell – his scheduled third-round opponent – withdrew due to injury.

READ: Vukic, O’Connell, De Minaur reach third round in Toronto

Aleksandar Vukic faces American Frances Tiafoe on Friday in a rematch of their 2024 encounter in Almaty, Kazakhstan. The Australian defeated Tiafoe 6-2 7-6(11) to reach his second-career ATP semifinal.

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