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| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 4 - Oct. 15 | Seed: 19 |
| Round | Opponent | W / L | Result |
| First Round | Bye |
| US Open | ||
| Surface: Hard | Date: Aug. 28 - Sep. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pedro Cachin | Win | 1-6, 6-3, 6-2, 6-4 |
| Second Round | Dominic Thiem | Win | 7-6 (7-1), 1-0 Retired |
| Third Round | Aslan Karatsev | Win | 6-4, 3-6, 6-2, 6-0 |
| Fourth Round | Tommy Paul | Win | 6-4, 6-3, 4-6, 6-4 |
| Quarterfinals | Frances Tiafoe | Win | 6-2, 3-6, 7-6 (9-7), 6-2 |
| Semifinals | Novak Djokovic | Loss | 3-6, 2-6, 6-7 (4-7) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 13 - Aug. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher Eubanks | Win | 5-7, 6-4, 6-4 |
| Second Round | Stefanos Tsitsipas | Loss | 6-7 (3-7), 6-7 (2-7) |
| Omnium National Bank presented by Rogers | ||
| Surface: Hard | Date: Aug. 7 - Aug. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Bernabe Zapata Miralles | Win | 7-6 (7-1), 6-4 |
| Second Round | Carlos Alcaraz | Loss | 3-6, 6-7 (3-7) |
| Citi Open | ||
| Surface: Hard | Date: Jul. 31 - Aug. 6 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Juncheng Shang | Loss | 2-6, 6-3, 3-6 |
| Truist Atlanta Open presented by Fiserv | ||
| Surface: Hard | Date: Jul. 24 - Jul. 30 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Juncheng Shang | Loss | 4-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 3 - Jul. 16 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Taro Daniel | Win | |
| Second Round | Laslo Djere | Loss |
| Mallorca Championships | ||
| Surface: Grass | Date: Jun. 25 - Jul. 1 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Christopher Eubanks | Loss |
| Cinch Championships | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | J.J. Wolf | Win | |
| Second Round | Lorenzo Musetti | Loss |
| French Open | ||
| Surface: Red Clay | Date: May 28 - Jun. 11 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Sonego | Loss |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 21 - May 27 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Loss |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 10 - May 21 | Seed: 28 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alexander Bublik | Loss |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 26 - May 7 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jan-Lennard Struff | Loss |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 17 - Apr. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mackenzie McDonald | Win | |
| Second Round | Casper Ruud | Loss |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 9 - Apr. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 3 - Apr. 9 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Constant Lestienne | Win | |
| Second Round | Dominic Thiem | Loss |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 2 | Seed: 32 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Adrian Mannarino | Loss |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fabio Fognini | Win | |
| Second Round | Taylor Fritz | Loss |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 26 - Mar. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Holger Rune | Loss |
| Delray Beach Open | ||
| Surface: Hard | Date: Feb. 13 - Feb. 19 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Marcos Giron | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Zhizhen Zhang | Win | |
| Second Round | Nicolas Jarry | Win | |
| Third Round | Alexei Popyrin | Win | |
| Fourth Round | J.J. Wolf | Win | |
| Quarterfinals | Tommy Paul | Loss |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 9 - Jan. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Baez | Win | |
| Second Round | Quentin Halys | Loss |
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