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| Sofia Open | ||
| Surface: Hard | Date: Nov. 8 - Nov. 14 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Vasek Pospisil | Loss | 3-6, 4-6 |
| Rolex Paris Masters | ||
| Surface: Hard | Date: Nov. 2 - Nov. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 6-4, 6-2 |
| Second Round | Pablo Carreno Busta | Loss | 6-7 (3-7), 2-6 |
| Erste Bank Open 500 | ||
| Surface: Hard | Date: Oct. 26 - Nov. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Loss | 7-6 (7-3), 3-6, 4-6 |
| bett1HULKS Championships | ||
| Surface: Hard | Date: Oct. 19 - Oct. 25 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | 6-3, 6-1 |
| Second Round | Yoshihito Nishioka | Loss | 6-2, 3-6, 6-7 (3-7) |
| bett1HULKS Indoors | ||
| Surface: Hard | Date: Oct. 12 - Oct. 18 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Oscar Otte | Loss | 4-6, 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: Sep. 27 - Oct. 11 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Frances Tiafoe | Win | 3-6, 7-6 (7-5), 6-3, 6-7(2-7), 6-3 |
| Second Round | Daniel Altmaier | Loss | 3-6, 6-7 (4-7), 3-6 |
| Hamburg European Open | ||
| Surface: Red Clay | Date: Sep. 21 - Sep. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Loss | 6-7 (5-7), 6-4, 5-7 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: Sep. 14 - Sep. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Federico Coria | Loss | 1-6, 6-7 (5-7) |
| US Open | ||
| Surface: Hard | Date: Aug. 31 - Sep. 13 | Seed: 28 |
| Round | Opponent | W / L | Result |
| First Round | Pedro Martinez | Win | 6-0, 7-5, 6-4 |
| Second Round | Michael Mmoh | Win | 6-2, 6-2, 7-5 |
| Third Round | Novak Djokovic | Loss | 3-6, 3-6, 1-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex De Minaur | Win | 6-2, 6-4 |
| Second Round | Denis Shapovalov | Win | 7-6 (7-4), 3-6, 6-4 |
| Third Round | David Goffin | Win | 6-4, 3-6, 6-4 |
| Quarterfinals | Novak Djokovic | Loss | 3-6, 1-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 24 - Feb. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Roberto Bautista Agut | Win | 7-6 (7-2), 7-5 |
| Second Round | Nikoloz Basilashvili | Win | 6-1, 6-0 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 6-4, 4-6, 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 10 - Feb. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Loss | 3-6, 6-1, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 20 - Feb. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Novak Djokovic | Loss | 6-7 (5-7), 2-6, 6-2, 1-6 |
| Adelaide International | ||
| Surface: Hard | Date: Jan. 12 - Jan. 18 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Salvatore Caruso | Win | 6-4, 6-2 |
| Second Round | Alex Bolt | Loss | 3-6, 4-6 |
