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| US Open | ||
| Surface: Hard | Date: Aug. 28 - Sep. 10 | Seed: 28 |
| Round | Opponent | W / L | Result |
| First Round | SoonWoo Kwon | Win | 6-3, 6-4, 0-6, 6-4 |
| Second Round | Benjamin Bonzi | Loss | 6-7 (6-8), 6-2, 2-6, 6-7 (7-9) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 13 - Aug. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ben Shelton | Loss | 7-5, 4-6, 4-6 |
| Omnium National Bank presented by Rogers | ||
| Surface: Hard | Date: Aug. 7 - Aug. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Loss | 6-7 (3-7), 7-6 (7-4), 1-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 31 - Aug. 6 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Sho Shimabukuro | Win | 6-3, 6-4 |
| Third Round | Jordan Thompson | Loss | 2-6, 2-6 |
| Truist Atlanta Open presented by Fiserv | ||
| Surface: Hard | Date: Jul. 24 - Jul. 30 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Andres Martin | Win | 6-2, 6-4 |
| Second Round | Brandon Nakashima | Win | 6-7 (4-7), 6-4, 7-5 |
| Quarterfinals | Aleksandar Vukic | Loss | 4-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 3 - Jul. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thiago Monteiro | Win | |
| Second Round | Cameron Norrie | Win | |
| Third Round | Christopher O'Connell | Win | |
| Fourth Round | Stefanos Tsitsipas | Win | |
| Quarterfinals | Daniil Medvedev | Loss |
| Mallorca Championships | ||
| Surface: Grass | Date: Jun. 25 - Jul. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex Michelsen | Win | |
| Second Round | Ben Shelton | Win | |
| Quarterfinals | Arthur Rinderknech | Win | |
| Semifinals | Lloyd Harris | Win | |
| Final | Adrian Mannarino | Win |
| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Loss |
| Boss Open | ||
| Surface: Grass | Date: Jun. 12 - Jun. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Loss |
| French Open | ||
| Surface: Red Clay | Date: May 28 - Jun. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Holger Rune | Loss |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 21 - May 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benoit Paire | Win | |
| Second Round | Alexander Zverev | Loss |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Win | |
| Second Round | Borna Coric | Win | |
| Third Round | Gregoire Barrere | Win | |
| Fourth Round | Adrian Mannarino | Win | |
| Quarterfinals | Daniil Medvedev | Loss |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 26 - Mar. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Feliciano Lopez | Loss |
| Delray Beach Open | ||
| Surface: Hard | Date: Feb. 13 - Feb. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aleksandar Vukic | Loss |
| Dallas Open | ||
| Surface: Hard | Date: Feb. 6 - Feb. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Oscar Otte | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | SoonWoo Kwon | Win | |
| Second Round | Jiri Lehecka | Loss |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 9 - Jan. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Win | |
| Second Round | David Goffin | Loss |
