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| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jordan Thompson | Win | 7-5, 6-2 |
| Second Round | Lorenzo Sonego | Win | 7-6 (9-7), 7-6 (7-3) |
| Third Round | Gael Monfils | Loss | 5-7, 2-6 |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Loss | 6-7 (11-13), 5-7 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jiri Vesely | Win | 7-6 (7-1), 4-6, 3-6, 7-6(7-5), 7-6 (7-4) |
| Second Round | Diego Schwartzman | Loss | 6-7 (4-7), 3-6, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Loss | 2-6, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Aug. 2 - Aug. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jenson Brooksby | Loss | 6-7 (4-7), 3-6 |
| Truist Atlanta Open | ||
| Surface: Hard | Date: Jul. 26 - Aug. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nick Kyrgios | Loss | 6-7 (4-7), 3-6 |
| Hall of Fame Open | ||
| Surface: Grass | Date: Jul. 12 - Jul. 18 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Illya Marchenko | Win | 7-5, 6-3 |
| Second Round | Sebastian Ofner | Win | 7-5, 7-6 (7-3) |
| Quarterfinals | Jack Sock | Win | 6-7 (5-7), 6-2, 6-4 |
| Semifinals | Alexander Bublik | Win | 4-6, 7-6 (7-3), 7-5 |
| Final | Jenson Brooksby | Win | 7-6 (10-8), 6-4 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marcelo Tomas Barrios Vera | Win | 6-7 (4-7), 6-4, 6-4, 7-6(7-4) |
| Second Round | Novak Djokovic | Loss | 3-6, 3-6, 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Soon Woo Kwon | Loss | 5-7, 4-6, 6-2, 6-7 (4-7) |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Frances Tiafoe | Win | 4-6, 7-6 (8-6), 7-6 (7-4) |
| Second Round | Roberto Carballes Baena | Win | 6-3, 7-6 (7-4) |
| Quarterfinals | Marin Cilic | Loss | 6-7 (7-9), 0-0 Retired |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Loss | 6-7 (6-8), 5-7 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Loss | 6-7 (9-11), 5-7, 3-6 |
| Great Ocean Road Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Feliciano Lopez | Win | 6-4, 7-5 |
| Second Round | Cedrik-Marcel Stebe | Win | 6-4, 6-2 |
| Third Round | Karen Khachanov | Loss | 3-6, 6-7 (5-7) |
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