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| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: Sep. 14 - Sep. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Rafael Nadal | Loss | 1-6, 1-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 31 - Sep. 13 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Yasutaka Uchiyama | Win | 4-6, 6-3, 1-6, 6-3, 6-3 |
| Second Round | Mitchell Krueger | Win | 6-1, 6-2, 6-2 |
| Third Round | Ricardas Berankis | Win | 6-4, 6-3, 6-2 |
| Fourth Round | Novak Djokovic | Win | 6-5 Retired |
| Quarterfinals | Denis Shapovalov | Win | 3-6, 7-6 (7-5), 7-6 (7-4), 0-6, 6-3 |
| Semifinals | Alexander Zverev | Loss | 6-3, 6-2, 3-6, 4-6, 3-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 7-5, 6-1 |
| Second Round | Karen Khachanov | Loss | 6-7 (8-10), 1-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 24 - Feb. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Loss | 6-7 (1-7), 1-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 10 - Feb. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Adrian Mannarino | Win | 7-5, 6-7 (3-7), 6-4 |
| Second Round | Roberto Bautista Agut | Win | 6-4, 2-6, 7-6 (7-4) |
| Quarterfinals | Jannik Sinner | Win | 7-5, 3-6, 7-6 (8-6) |
| Semifinals | Felix Auger-Aliassime | Loss | 6-7 (2-7), 4-6 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 3 - Feb. 9 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Norbert Gombos | Loss | 6-3, 4-6, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 20 - Feb. 2 | Seed: 27 |
| Round | Opponent | W / L | Result |
| First Round | Jozef Kovalik | Win | 6-4, 3-6, 6-1, 7-6(7-2) |
| Second Round | Peter Gojowczyk | Win | 6-4, 6-1, 1-6, 6-4 |
| Third Round | Rafael Nadal | Loss | 1-6, 2-6, 4-6 |
| Adelaide International | ||
| Surface: Hard | Date: Jan. 12 - Jan. 18 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jeremy Chardy | Win | 6-3, 6-2 |
| Quarterfinals | Lloyd Harris | Loss | 3-6, 3-6 |
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