| ||||||||||||||
| BOSS OPEN | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher O'Connell | Win | 6-4, 6-3 |
| Second Round | Alexander Bublik | Win | 6-3, 7-6 (7-4) |
| Quarterfinals | Stefanos Tsitsipas | Win | 7-6 (7-4), 6-3 |
| Semifinals | Nick Kyrgios | Win | 7-6 (7-5), 6-2 |
| Final | Matteo Berrettini | Loss | 4-6, 7-5, 3-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dominic Thiem | Win | 6-3, 6-4 |
| Second Round | Denis Shapovalov | Win | 6-1, 3-6, 6-2 |
| Third Round | Novak Djokovic | Loss | Retired |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Federico Delbonis | Win | 7-6 (7-4), 6-1 |
| Second Round | Daniil Medvedev | Loss | 4-6, 2-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taro Daniel | Win | 1-6, 6-2, 6-4 |
| Second Round | Alexander Bublik | Loss | 6-7 (9-11), 3-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher O'Connell | Win | 6-7 (4-7), 6-3, 7-5 |
| Second Round | Jannik Sinner | Loss | 5-7, 2-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Feb. 14 - Feb. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taro Daniel | Win | 6-2, 6-2 |
| Second Round | Roberto Bautista Agut | Loss | 0-6, 1-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Bublik | Win | 7-6 (8-6), 6-4 |
| Second Round | Felix Auger-Aliassime | Loss | 3-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 6-1, 3-6, 6-4, 6-7(5-7), 6-4 |
| Second Round | Taro Daniel | Loss | 4-6, 4-6, 4-6 |
| Sydney Tennis Classic | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Viktor Durasovic | Win | 6-3, 6-1 |
| Second Round | Nikoloz Basilashvili | Win | 6-7 (4-7), 7-6 (7-3), 6-3 |
| Quarterfinals | David Goffin | Win | 6-2, 0-0 Retired |
| Semifinals | Reilly Opelka | Win | 6-7 (6-8), 6-4, 6-4 |
| Final | Aslan Karatsev | Loss | 3-6, 3-6 |
| Melbourne Summer Set 1 | ||
| Surface: Hard | Date: Jan. 4 - Jan. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Facundo Bagnis | Loss | 3-6, 7-5, 3-6 |
