| ||||||||||||||
| China Open | ||
| Surface: Hard | Date: Sep. 28 - Oct. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Sonego | Win | 7-5, 3-6, 6-0 |
| Second Round | Andrey Rublev |
| US Open | ||
| Surface: Hard | Date: Aug. 28 - Sep. 10 | Seed: 29 |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Loss | 4-6, 2-6, 2-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 13 - Aug. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Arthur Fils | Win | 6-4, 3-6, 6-2 |
| Second Round | Tommy Paul | Loss | 1-6, 6-7 (4-7) |
| Omnium National Bank presented by Rogers | ||
| Surface: Hard | Date: Aug. 7 - Aug. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Jarry | Win | 4-6, 6-3, 6-4 |
| Second Round | Taylor Fritz | Loss | 6-7 (7-9), 6-3, 3-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 31 - Aug. 6 | Seed: 13 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Thanasi Kokkinakis | Win | 7-6 (8-6), 1-6, 6-4 |
| Third Round | Yosuke Watanuki | Win | 6-0, 6-2 |
| Quarterfinals | Grigor Dimitrov | Loss | Retired |
| Truist Atlanta Open presented by Fiserv | ||
| Surface: Hard | Date: Jul. 24 - Jul. 30 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Constant Lestienne | Win | 4-6, 7-5, 7-5 |
| Second Round | Lloyd Harris | Win | 7-6 (8-6), 6-4 |
| Quarterfinals | Alex De Minaur | Win | 7-6 (7-4), 6-3 |
| Semifinals | Aleksandar Vukic | Loss | 6-3, 6-7 (2-7), 5-7 |
| Infosys Hall of Fame Open | ||
| Surface: Grass | Date: Jul. 17 - Jul. 23 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Steve Johnson | Win | |
| Quarterfinals | Kevin Anderson | Win | |
| Semifinals | Adrian Mannarino | Loss |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 3 - Jul. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jason Kubler | Loss |
| Cinch Championships | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ryan Peniston | Loss |
| Libema Open | ||
| Surface: Grass | Date: Jun. 12 - Jun. 18 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Jason Kubler | Win | |
| Second Round | Emil Ruusuvuori | Loss |
| French Open | ||
| Surface: Red Clay | Date: May 28 - Jun. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Adrian Mannarino | Win | |
| Second Round | Lorenzo Sonego | Loss |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 10 - May 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Emil Ruusuvuori | Loss |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 26 - May 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Emil Ruusuvuori | Loss |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 17 - Apr. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher O'Connell | Loss |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 9 - Apr. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Sonego | Loss |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Win | |
| Second Round | Miomir Kecmanovic | Loss |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Bernabe Zapata Miralles | Win | |
| Second Round | Denis Shapovalov | Win | |
| Third Round | Andrey Rublev | Loss |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 6 - Feb. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Davidovich Fokina | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Win | |
| Second Round | Denis Kudla | Win | |
| Third Round | Holger Rune | Loss |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 9 - Jan. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher Eubanks | Loss |
