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| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Yoshihito Nishioka | Win | 6-3, 6-4 |
| Third Round | Jannik Sinner | Loss | Retired |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 19 |
| Round | Opponent | W / L | Result |
| First Round | Brandon Nakashima | Loss | 6-7 (7-9), 6-7 (6-8), 3-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Cameron Norrie | Win | 4-6, 7-6 (7-5), 6-4 |
| Second Round | Jannik Sinner | Win | 5-7, 7-6 (7-4), 6-4 |
| Third Round | Benoit Paire | Loss | 6-7 (1-7), 7-6 (7-2), 1-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Davidovich Fokina | Win | 6-4, 6-1 |
| Second Round | Cristian Garin | Win | 4-6, 6-3, 6-4 |
| Third Round | Andrey Rublev | Win | 7-5, 7-6 (7-5) |
| Quarterfinals | Gael Monfils | Win | 7-6 (7-5), 6-4 |
| Semifinals | Daniil Medvedev | Loss | 2-6, 2-6 |
| Truist Atlanta Open | ||
| Surface: Hard | Date: Jul. 26 - Aug. 1 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | J.J. Wolf | Win | 6-4, 6-7 (3-7), 6-4 |
| Second Round | Jack Sock | Win | 7-6 (8-6), 6-4 |
| Quarterfinals | Christopher O'Connell | Win | 7-6 (7-5), 6-7 (3-7), 6-4 |
| Semifinals | Taylor Fritz | Win | 7-6 (7-4), 5-7, 6-3 |
| Final | Brandon Nakashima | Win | 7-6 (10-8), 7-5 |
| Mifel Open | ||
| Surface: Hard | Date: Jul. 19 - Jul. 25 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Evgeny Donskoy | Win | 7-5, 3-6, 7-6 (7-5) |
| Quarterfinals | Alex Bolt | Win | 6-3, 6-4 |
| Semifinals | Brandon Nakashima | Loss | 5-7, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 28 |
| Round | Opponent | W / L | Result |
| First Round | Yoshihito Nishioka | Loss | 6-7 (5-7), 6-2, 3-6, 7-6 (7-3), 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: 31 |
| Round | Opponent | W / L | Result |
| First Round | Sam Querrey | Win | 7-6 (7-2), 6-3, 6-4 |
| Second Round | Filip Krajinovic | Win | 7-6 (8-6), 6-1, 7-6 (7-5) |
| Third Round | Stefanos Tsitsipas | Loss | 7-5, 3-6, 6-7 (3-7), 1-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Miomir Kecmanovic | Win | 6-4, 7-6 (8-6) |
| Second Round | Roberto Bautista Agut | Win | 6-4, 6-7 (4-7), 7-6 (8-6) |
| Third Round | Andrey Rublev | Win | 7-6 (7-4), 3-6, 7-6 (7-4) |
| Quarterfinals | Dominic Thiem | Loss | 6-3, 3-6, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mackenzie McDonald | Win | 2-6, 6-3, 7-5 |
| Third Round | Felix Auger-Aliassime | Win | 7-6 (7-5), 7-6 (7-5) |
| Fourth Round | Roberto Bautista Agut | Loss | 3-6, 6-4, 6-7 (7-9) |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Salvatore Caruso | Win | 6-4, 6-3 |
| Second Round | Stefanos Tsitsipas | Loss | 3-6, 2-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Thiago Monteiro | Win | 6-4, 7-6 (7-4) |
| Quarterfinals | Sebastian Korda | Loss | 3-6, 6-4, 3-6 |
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