Karen Khachanov continues to impress in Toronto as he looks to take advantage of the weakened draw.
Three Grand Slam champions, Novak Djokovic, Carlos Alcaraz, and Jannik Sinner, all withdrew from the Canadian Open before the tournament began, as they chose to rest up after their Wimbledon exploits.
Skipping the event, the trio provided the rest of the ATP Tour with a golden opportunity to win a Masters 1000 title in their absence.
Making the most of the opportunity, Russian star Khachanov has made a positive start in Canada, knocking out Juan Pablo Ficovich, Emilio Nava, Casper Ruud, and Alex Michelsen en route to the semifinals.
He will now take on Germany’s Alexander Zverev for a place in the final, the man he lost to twice in 2024.
Reflecting on those two defeats, Khachanov highlighted what Zverev did that surprised him when they played in Miami and Cincinnati last year.
Karen Khachanov says Alexander Zverev played ‘quite aggressively’ against him in 2024
Speaking to Russian media outlet ‘Bolshe!’ after his quarterfinal win at the Canadian Open, Khachanov shared his thoughts on Zverev and their previous encounters.
“Last year I lost to him twice, I think, and both times they were pretty comfortable, no chance,” he said.
“He has a big, strong first serve and plays good defense.
“In those matches with me, I remember him playing quite aggressively, which I did not expect, both in Miami and Cincinnati.
“Now, it’s a different tournament, a different year, a different moment. Therefore, I need to prepare, try to show my best level, and build on that to see what will work out.”
Zverev secured his fourth and fifth wins over Khachanov in 2024, extending his head-to-head advantage to 5-2.
| Match | Winner | Loser | Score |
| 2024 Cincinnati Open – 2R | Alexander Zverev | Karen Khachanov | 6-3, 6-2 |
| 2024 Miami Open – 4R | Alexander Zverev | Karen Khachanov | 6-1, 6-4 |
| 2021 Olympics – F | Alexander Zverev | Karen Khachanov | 6-3, 6-1 |
| 2019 Canadian Open – QF | Karen Khachanov | Alexander Zverev | 6-3, 6-3 |
| 2018 Paris Masters – QF | Karen Khachanov | Alexander Zverev | 6-1, 6-2 |
| 2018 French Open – 4R | Alexander Zverev | Karen Khachanov | 4-6, 7-6, 2-6, 6-3, 6-3 |
| 2016 St Petersburg – 1R | Alexander Zverev | Karen Khachanov | 7-6, 6-4 |
The Russian hasn’t beaten Zverev since 2019, when he secured the win in straight sets to advance to the Canadian Open quarterfinals.
Khachanov noted that he was surprised by Zverev’s aggression in their two 2024 encounters, a statement that may seem confusing to those who’ve watched the world number three play recently.
In 2025, Zverev has been often criticized for playing too ‘passively’, with some suggesting his lack of aggression has cost him chances at Grand Slam success over the years.
It remains to be seen how Zverev will approach their semifinal tie in Toronto, but Khachanov will no doubt be well-prepared, as he looks to avoid a fourth consecutive defeat.
Neither player will want to fall short, as they currently sit just two wins away from a first Masters 1000 title of the season.
Who else remains in the Canadian Open draw?
Khachanov and Zverev will contest the first semifinal, but who remains alive in the bottom half of the draw?
- [9] Alex de Minaur v [4] Ben Shelton
- [6] Andrey Rublev v [2] Taylor Fritz
One of Alex de Minaur, Ben Shelton, Andrey Rublev, or Taylor Fritz will make their way through to Thursday’s final to take on the winner of Khachanov/Zverev.
Of the six players remaining, four have won Masters 1000 titles, although one player has enjoyed far more success than the rest.
| Player | Round | ATP Ranking | Age | Masters 1000 titles | Most recent Masters 1000 title |
| Alexander Zverev | SF | 3rd | 28 | 7 | 2024 Paris Masters |
| Karen Khachanov | SF | 16th | 29 | 1 | 2018 Paris Masters |
| Alex de Minaur | QF | 8th | 26 | 0 | – |
| Ben Shelton | QF | 7th | 22 | 0 | – |
| Andrey Rublev | QF | 11th | 27 | 2 | 2024 Madrid Open |
| Taylor Fritz | QF | 4th | 27 | 1 | 2022 Indian Wells |
Seven times a Masters 1000 champion, no player left in the field has more experience at this level than Zverev.
Searching for his eighth Masters 1000 title in Toronto, Zverev will be tough to beat, although that’s not to say he won’t face some stiff opposition.
The two players yet to win a Masters 1000 could well be his greatest threat, as both De Minaur and Shelton look to be hitting form at the right time.
De Minaur has already contested a Canadian Open final in his career, losing out to Jannik Sinner two years ago, and would surely love to go one better this time around.
Shelton has been patiently waiting for his moment to strike, and with three big names missing in Toronto, this may just be the 22-year-old’s time to shine.
Only time will tell who will emerge victorious in Canada, but you certainly won’t want to miss any of the action.
The final two quarterfinal ties will take place on Tuesday, August 5.
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