| ||||||||||||||
| Chengdu Open | ||
| Surface: Hard | Date: Sep. 20 - Sep. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Max Purcell | Win | 6-2, 7-6 (10-8) |
| Second Round | Dusan Lajovic | Win | 6-1, 7-6 (7-1) |
| Quarterfinals | Roman Safiullin | Loss | 6-7 (1-7), 0-0 Retired |
| US Open | ||
| Surface: Hard | Date: Aug. 28 - Sep. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Botic Van De Zandschulp | Loss | 3-6 Retired |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 13 - Aug. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Isner | Win | 7-6 (7-5), 7-6 (7-2) |
| Second Round | Carlos Alcaraz | Loss | 5-7, 6-4, 3-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 31 - Aug. 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kevin Anderson | Win | 6-4, 6-7 (1-7), 6-1 |
| Second Round | Adrian Mannarino | Win | 7-5, 6-4 |
| Third Round | Christopher Eubanks | Win | 6-2, 6-2 |
| Quarterfinals | Taylor Fritz | Loss | 3-6, 3-6 |
| Truist Atlanta Open presented by Fiserv | ||
| Surface: Hard | Date: Jul. 24 - Jul. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kei Nishikori | Loss | 6-7 (5-7), 6-7 (5-7) |
| Infosys Hall of Fame Open | ||
| Surface: Grass | Date: Jul. 17 - Jul. 23 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Aleksandar Kovacevic | Win | |
| Second Round | Liam Broady | Win | |
| Quarterfinals | Adrian Mannarino | Loss |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 3 - Jul. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Brandon Nakashima | Win | |
| Second Round | Novak Djokovic | Loss |
| Mallorca Championships | ||
| Surface: Grass | Date: Jun. 25 - Jul. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Win | |
| Second Round | Feliciano Lopez | Loss |
| Cinch Championships | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Win | |
| Second Round | Cameron Norrie | Loss |
| Libema Open | ||
| Surface: Grass | Date: Jun. 12 - Jun. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Giovanni Mpetshi Perricard | Win | |
| Second Round | Milos Raonic | Win | |
| Quarterfinals | Adrian Mannarino | Win | |
| Semifinals | Rinky Hijikata | Win | |
| Final | Tallon Griekspoor | Loss |
| French Open | ||
| Surface: Red Clay | Date: May 28 - Jun. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Max Purcell | Loss |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 17 - Apr. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Flavio Cobolli | Loss |
| Fayez Sarofim & Co. U.S. Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 3 - Apr. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | J.J. Wolf | Loss |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex Molcan | Loss |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Win | |
| Second Round | Stefanos Tsitsipas | Win | |
| Third Round | Alejandro Tabilo | Loss |
| Delray Beach Open | ||
| Surface: Hard | Date: Feb. 13 - Feb. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Loss |
| Dallas Open | ||
| Surface: Hard | Date: Feb. 6 - Feb. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Win | |
| Second Round | Adrian Mannarino | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | J.J. Wolf | Loss |
| Adelaide International 1 | ||
| Surface: Hard | Date: Jan. 1 - Jan. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Quentin Halys | Loss |
