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| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Win | 6-7 (5-7), 6-3, 6-2 |
| Second Round | Daniel Evans | Loss | 6-4, 3-6, 4-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Salvatore Caruso | Win | 6-1, 6-1, 5-7, 6-3 |
| Second Round | Mackenzie McDonald | Win | 7-6 (7-3), 6-3, 6-7 (5-7), 2-6, 6-3 |
| Third Round | Novak Djokovic | Loss | 7-6 (7-4), 3-6, 3-6, 2-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Miomir Kecmanovic | Win | 6-4, 6-7 (5-7), 6-2 |
| Second Round | Hubert Hurkacz | Loss | Retired |
| Citi Open | ||
| Surface: Hard | Date: Aug. 2 - Aug. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sam Querrey | Win | 6-4, 6-3 |
| Second Round | Alexander Bublik | Win | 6-2, 7-5 |
| Third Round | Cameron Norrie | Win | 3-6, 6-3, 6-3 |
| Quarterfinals | Lloyd Harris | Win | 6-3, 7-5 |
| Semifinals | Mackenzie McDonald | Loss | 4-6, 6-3, 5-7 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Win | 6-4, 6-4, 6-4 |
| Second Round | Jordan Thompson | Loss | 5-7, 4-6, 7-5, 3-6 |
| NOVENTI OPEN | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Win | 6-3, 2-6, 6-2 |
| Second Round | Sebastian Korda | Loss | 6-2, 3-6, 5-7 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alessandro Giannessi | Win | 6-4, 6-7 (4-7), 6-3, 4-6, 6-4 |
| Second Round | Karen Khachanov | Win | 4-6, 6-2, 2-6, 6-4, 6-4 |
| Third Round | Henri Laaksonen | Win | 7-5, 0-0 Retired |
| Fourth Round | Alexander Zverev | Loss | 4-6, 1-6, 1-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fabio Fognini | Win | 6-3, 6-4 |
| Second Round | Pablo Carreno Busta | Win | Retired |
| Third Round | Alexander Zverev | Loss | 6-4, 3-6, 4-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Win | 6-7 (6-8), 6-2, 6-2 |
| Second Round | Alexander Zverev | Loss | 3-6, 2-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Win | 4-6, 7-6 (7-4), 6-2 |
| Second Round | Cristian Garin | Win | 7-6 (7-5), 4-6, 6-1 |
| Third Round | Rafael Nadal | Loss | 0-6, 6-2, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 28 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Aljaz Bedene | Win | 7-6 (8-6), 5-7, 6-4 |
| Third Round | Stefanos Tsitsipas | Loss | 3-6, 6-3, 1-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Mar. 14 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Win | 3-6, 6-3, 6-4 |
| Second Round | David Goffin | Win | 6-3, 7-6 (7-3) |
| Third Round | Aljaz Bedene | Win | 6-4, 6-4 |
| Quarterfinals | Lloyd Harris | Loss | 1-6, 6-3, 3-6 |
| Open 13 Provence | ||
| Surface: Hard | Date: Mar. 8 - Mar. 14 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Loss | 1-6, 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Mar. 1 - Mar. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Win | 7-6 (7-4), 6-1 |
| Second Round | Alex De Minaur | Win | 6-3, 2-6, 7-5 |
| Quarterfinals | Borna Coric | Loss | 6-7 (2-7), 6-7 (4-7) |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pablo Carreno Busta | Loss | 5-7, 6-7 (4-7), 2-6 |
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