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| French Open | ||
| Surface: Red Clay | Date: May 28 - Jun. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Loss | 4-6, 7-6 (9-7), 6-2, 6-7 (4-7), 6-7 (4-10) |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 26 - May 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Win | 4-6, 6-4, 6-4 |
| Second Round | Roberto Bautista Agut | Loss | 6-4, 6-7 (5-7), 3-6 |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 17 - Apr. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Sonego | Loss | 6-3, 6-7 (5-7), 5-7 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 3 - Apr. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nuno Borges | Win | 6-3, 6-4 |
| Second Round | Roberto Bautista Agut | Win | 7-6 (7-5), 7-5 |
| Quarterfinals | Dominic Thiem | Win | 6-1, 6-4 |
| Semifinals | Casper Ruud | Loss | 4-6, 6-3, 6-7 (2-7) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pedro Martinez | Win | 6-2, 7-6 (7-4) |
| Second Round | Alex De Minaur | Win | 6-7 (5-7), 7-6 (7-3), 7-6 (10-8) |
| Third Round | Mackenzie McDonald | Win | 7-6 (7-2), 6-3 |
| Fourth Round | Daniil Medvedev | Loss | 4-6, 2-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Loss | 6-1, 3-6, 3-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 27 - Mar. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thanasi Kokkinakis | Loss | 4-6, 6-7 (9-11) |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Feb. 20 - Feb. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tallon Griekspoor | Loss | 6-7 (4-7), 6-4, 6-7 (5-7) |
| ABN Amro World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 13 - Feb. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Botic Van De Zandschulp | Loss | 7-5, 4-6, 6-7 (4-7) |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 6 - Feb. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Clement Chidekh | Win | |
| Second Round | Alejandro Davidovich Fokina | Win | |
| Quarterfinals | Arthur Fils | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Loss |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 9 - Jan. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex Molcan | Win | |
| Second Round | Ben Shelton | Win | |
| Quarterfinals | Jenson Brooksby | Loss |
| Adelaide International 1 | ||
| Surface: Hard | Date: Jan. 1 - Jan. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jordan Thompson | Win | |
| Second Round | Novak Djokovic | Loss |
