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| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 8 - Aug. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Baez |
| Citi Open | ||
| Surface: Hard | Date: Aug. 1 - Aug. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marcos Giron | Win | 6-3, 6-2 |
| Second Round | Tommy Paul | Win | 6-3, 6-4 |
| Third Round | Reilly Opelka | Win | 7-6 (7-1), 6-2 |
| Quarterfinals | Frances Tiafoe | Win | 6-7 (5-7), 7-6 (14-12), 6-2 |
| Semifinals | Mikael Ymer | Win | 7-6 (7-4), 6-3 |
| Final | Yoshihito Nishioka | Win | 6-4, 6-3 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Paul Jubb | Win | 3-6, 6-1, 7-5, 6-7(3-7), 7-5 |
| Second Round | Filip Krajinovic | Win | 6-2, 6-3, 6-1 |
| Third Round | Stefanos Tsitsipas | Win | 6-7 (2-7), 6-4, 6-3, 7-6(9-7) |
| Fourth Round | Brandon Nakashima | Win | 4-6, 6-4, 7-6 (7-2), 3-6, 6-2 |
| Quarterfinals | Cristian Garin | Win | 6-4, 6-3, 7-6 (7-5) |
| Semifinals | Rafael Nadal | Win | Retired |
| Final | Novak Djokovic | Loss | 6-4, 3-6, 4-6, 6-7 (3-7) |
| Mallorca Championships | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 5-7, 7-6 (7-1), 7-6 (7-1) |
| Second Round | Roberto Bautista Agut | Loss | Retired |
| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Altmaier | Win | 6-3, 7-5 |
| Second Round | Stefanos Tsitsipas | Win | 5-7, 6-2, 6-4 |
| Quarterfinals | Pablo Carreno Busta | Win | 6-4, 6-2 |
| Semifinals | Hubert Hurkacz | Loss | 6-4, 6-7 (2-7), 6-7 (4-7) |
| BOSS OPEN | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jiri Lehecka | Win | 7-6 (7-3), 6-3 |
| Second Round | Nikoloz Basilashvili | Win | 6-7 (4-7), 6-4, 6-3 |
| Quarterfinals | Marton Fucsovics | Win | 7-6 (7-3), 3-0 Retired |
| Semifinals | Andy Murray | Loss | 6-7 (5-7), 2-6 |
| Fayez Sarofim & Co. US Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 4 - Apr. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mackenzie McDonald | Win | 4-6, 6-3, 6-4 |
| Second Round | Tommy Paul | Win | 6-4, 6-2 |
| Quarterfinals | Michael Mmoh | Win | Retired |
| Semifinals | Reilly Opelka | Loss | 3-6, 5-7 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Adrian Mannarino | Win | 7-6 (7-3), 6-3 |
| Second Round | Andrey Rublev | Win | 6-3, 6-0 |
| Third Round | Fabio Fognini | Win | 6-2, 6-4 |
| Fourth Round | Jannik Sinner | Loss | 6-7 (3-7), 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Baez | Win | 6-4, 6-0 |
| Second Round | Federico Delbonis | Win | 6-2, 6-2 |
| Third Round | Casper Ruud | Win | 6-4, 6-4 |
| Fourth Round | Jannik Sinner | Win | Retired |
| Quarterfinals | Rafael Nadal | Loss | 6-7 (0-7), 7-5, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Liam Broady | Win | 6-4, 6-4, 6-3 |
| Second Round | Daniil Medvedev | Loss | 6-7 (1-7), 4-6, 6-4, 2-6 |
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