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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benjamin Bonzi | Win | 7-6 (13-11), 3-6, 7-6 (7-4) |
| Second Round | Hubert Hurkacz | Win | 7-6 (7-5), 6-7 (5-7), 6-2 |
| Atlanta Open | ||
| Surface: Hard | Date: Jul. 25 - Jul. 31 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ben Shelton | Win | 7-6 (10-8), 4-6, 7-6 (7-3) |
| Quarterfinals | Jenson Brooksby | Loss | 6-3, 1-6, 4-6 |
| Infosys Hall of Fame Open | ||
| Surface: Grass | Date: Jul. 11 - Jul. 17 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Peter Gojowczyk | Win | 6-3, 7-6 (8-6) |
| Quarterfinals | Benjamin Bonzi | Win | 7-6 (7-2), 6-7 (6-8), 7-6 (7-5) |
| Semifinals | Maxime Cressy | Loss | 2-6, 6-4, 3-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Enzo Couacaud | Win | 6-7 (6-8), 7-6 (7-3), 4-6, 6-3, 7-5 |
| Second Round | Andy Murray | Win | 6-4, 7-6 (7-4), 6-7 (3-7), 6-4 |
| Third Round | Jannik Sinner | Loss | 4-6, 6-7 (4-7), 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 23 |
| Round | Opponent | W / L | Result |
| First Round | Quentin Halys | Win | 7-6 (7-3), 4-6, 7-6 (7-1), 7-6(8-6) |
| Second Round | Gregoire Barrere | Win | 6-4, 6-4, 3-6, 7-6(7-5) |
| Third Round | Bernabe Zapata Miralles | Loss | 4-6, 6-3, 4-6, 7-6 (7-5), 3-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Francisco Cerundolo | Win | 6-4, 6-3 |
| Second Round | Rafael Nadal | Loss | 3-6, 1-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Filip Krajinovic | Win | 7-6 (10-8), 6-4 |
| Second Round | Cameron Norrie | Loss | 4-6, 7-6 (7-5), 4-6 |
| Fayez Sarofim & Co. US Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 4 - Apr. 10 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Steve Johnson | Win | 6-7 (1-7), 7-6 (7-4), 6-3 |
| Quarterfinals | Frances Tiafoe | Win | 6-4, 2-6, 6-3 |
| Semifinals | Cristian Garin | Win | 4-6, 6-3, 6-4 |
| Final | Reilly Opelka | Loss | 3-6, 6-7 (7-9) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Hugo Gaston | Loss | 6-7 (5-7), 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 23 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Sam Querrey | Win | 7-6 (8-6), 7-6 (7-2) |
| Third Round | Diego Schwartzman | Win | 7-5, 6-3 |
| Fourth Round | Grigor Dimitrov | Loss | 3-6, 6-7 (6-8) |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fernando Verdasco | Win | 7-5, 6-7 (4-7), 7-6 (7-3) |
| Second Round | Cameron Norrie | Loss | 7-6 (7-2), 3-6, 4-6 |
| Dallas Open | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Kevin Anderson | Win | 7-6 (7-1), 6-7 (7-9), 7-6 (7-5) |
| Quarterfinals | Vasek Pospisil | Win | 6-4, 6-4 |
| Semifinals | Reilly Opelka | Loss | 6-7 (7-9), 6-7 (22-24) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Maxime Cressy | Loss | 6-7 (2-7), 5-7, 7-6 (7-4), 7-6 (7-4), 4-6 |
| Adelaide International 2 | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Thanasi Kokkinakis | Loss | 7-6 (7-5), 6-7 (5-7), 6-7 (4-7) |
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