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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 | Felix Auger-Aliassime | Win | 6-4, 7-5 |
| Second Round | Marco Cecchinato | Win | 6-4, 6-1 |
| Third Round | Novak Djokovic | Loss | 6-7 (7-9), 3-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 31 - Sep. 13 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Mikael Ymer | Win | 6-2, 7-6 (7-3), 6-3 |
| Second Round | Marcos Giron | Win | 6-4, 6-1, 6-3 |
| Third Round | David Goffin | Loss | 1-6, 6-7 (5-7), 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Salvatore Caruso | Win | 7-5, 6-4 |
| Second Round | Dominic Thiem | Win | 6-2, 6-1 |
| Third Round | Marton Fucsovics | Win | 6-2, 6-1 |
| Quarterfinals | Milos Raonic | Loss | 6-4, 6-7 (2-7), 5-7 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 24 - Feb. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Win | 4-6, 6-3, 6-3 |
| Second Round | Andrey Rublev | Loss | 6-7 (3-7), 0-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 10 - Feb. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tallon Griekspoor | Win | 6-4, 6-1 |
| Second Round | Vasek Pospisil | Win | 6-4, 7-6 (9-7) |
| Quarterfinals | Andrey Rublev | Win | 7-6 (7-2), 6-4 |
| Semifinals | Gael Monfils | Loss | 4-6, 6-7 (5-7) |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 3 - Feb. 9 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Enzo Couacaud | Win | 6-4, 6-4 |
| Second Round | Mikael Ymer | Win | 6-1, 6-1 |
| Quarterfinals | Gregoire Barrere | Win | 6-2, 7-5 |
| Semifinals | Gael Monfils | Loss | 6-7 (4-7), 2-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 20 - Feb. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Quentin Halys | Win | 7-6 (9-7), 7-6 (7-1), 3-6, 4-6, 7-5 |
| Second Round | Roger Federer | Loss | 1-6, 4-6, 1-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Jan. 6 - Jan. 11 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Kyle Edmund | Win | 4-6, 6-3, 6-3 |
| Second Round | Fernando Verdasco | Loss | 5-7, 6-4, 0-6 |
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