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| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Frances Tiafoe | Loss | 0-6, 4-6 |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tommy Paul | Win | 6-3, 5-7, 6-1 |
| Second Round | Lorenzo Sonego | Loss | 4-6, 3-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Loss | 2-6, 1-2 Retired |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 6-4, 6-4 |
| Second Round | Stefanos Tsitsipas | Loss | 6-7 (5-7), 3-6 |
| Citi Open | ||
| Surface: Hard | Date: Aug. 2 - Aug. 8 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Vasek Pospisil | Win | 7-5, 6-4 |
| Third Round | Jannik Sinner | Loss | 6-7 (3-7), 6-7 (3-7) |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex De Minaur | Win | 6-3, 6-4, 6-7 (5-7), 7-6(7-5) |
| Second Round | Antoine Hoang | Win | 7-5, 6-4, 6-4 |
| Third Round | Daniel Evans | Win | 6-3, 3-6, 6-3, 6-4 |
| Fourth Round | Karen Khachanov | Loss | 6-3, 4-6, 3-6, 7-5, 8-10 |
| NOVENTI OPEN | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Roberto Bautista Agut | Win | 6-3, 7-6 (7-0) |
| Second Round | Kei Nishikori | Win | 2-6, 6-3, 7-5 |
| Quarterfinals | Ugo Humbert | Loss | 2-6, 7-6 (7-5), 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pedro Martinez | Loss | 4-6, 2-6, 2-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 17 - May 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Win | 7-6 (7-5), 6-4 |
| Second Round | Lorenzo Musetti | Loss | 3-6, 6-1, 4-6 |
| Emilia-Romagna Open | ||
| Surface: Clay | Date: May 17 - May 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Win | 6-3, 6-4 |
| Second Round | Lorenzo Sonego | Win | 6-1, 7-5 |
| Quarterfinals | Yoshihito Nishioka | Win | 6-3, 6-3 |
| Semifinals | Tommy Paul | Win | 6-3, 6-3 |
| Final | Marco Cecchinato | Win | 6-2, 6-4 |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Elahi Galan | Loss | 1-6, 6-7 (7-9) |
| ATP Serbia Open | ||
| Surface: Red Clay | Date: Apr. 19 - Apr. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aljaz Bedene | Loss | 5-7, 6-1, 6-7 (5-7) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Radu Albot | Win | 6-3, 6-0 |
| Second Round | Fabio Fognini | Win | 1-6, 6-4, 6-2 |
| Third Round | Aslan Karatsev | Win | 6-3, 6-0 |
| Fourth Round | Diego Schwartzman | Win | 6-3, 4-6, 7-5 |
| Quarterfinals | Andrey Rublev | Loss | 5-7, 6-7 (7-9) |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marin Cilic | Win | 7-5, 6-2 |
| Second Round | Felix Auger-Aliassime | Loss | 3-6, 4-6 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 22 - Feb. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jo-Wilfried Tsonga | Win | 6-4, 6-2 |
| Second Round | Lorenzo Sonego | Loss | 3-6, 2-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Soon Woo Kwon | Win | 6-4, 6-4 |
| Second Round | Tommy Paul | Win | 4-6, 6-3, 6-2 |
| Quarterfinals | John Isner | Win | 6-3, 4-6, 6-3 |
| Semifinals | Cameron Norrie | Win | 6-3, 7-5 |
| Final | Hubert Hurkacz | Loss | 3-6, 3-6 |
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