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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jannik Sinner | Loss | 7-6 (11-9), 4-6, 6-7 (6-8) |
| Abierto de Tenis Mifel | ||
| Surface: Hard | Date: Aug. 1 - Aug. 6 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Fernando Verdasco | Win | 6-3, 6-7 (5-7), 6-2 |
| Second Round | Steve Johnson | Loss | 7-6 (7-3), 4-6, 4-6 |
| Atlanta Open | ||
| Surface: Hard | Date: Jul. 25 - Jul. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andres Martin | Loss | 3-6, 2-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kamil Majchrzak | Win | 7-6 (7-5), 6-2, 7-5 |
| Second Round | Novak Djokovic | Loss | 1-6, 4-6, 2-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Loss | 4-6, 6-4, 4-6, 6-7 (5-7) |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 15 - May 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fabio Fognini | Win | 6-4, 6-3 |
| Second Round | Federico Delbonis | Win | 1-6, 7-5, 7-5 |
| Quarterfinals | Casper Ruud | Loss | 4-6, 6-7 (3-7) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Win | 6-4, 6-2 |
| Second Round | Diego Schwartzman | Win | 4-6, 7-6 (7-3), 6-4 |
| Third Round | Denis Kudla | Win | 7-6 (7-5), 4-6, 7-6 (7-4) |
| Fourth Round | Alexander Zverev | Loss | 4-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Korda | Loss | 3-6, 4-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Korda | Loss | 4-6, 1-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yannick Hanfmann | Loss | 2-6, 3-6, 2-6 |
| Adelaide International 2 | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benoit Paire | Win | 6-4, 6-0 |
| Second Round | John Isner | Win | 6-7 (5-7), 7-6 (7-5), 7-6 (7-4) |
| Quarterfinals | Aleksandar Vukic | Win | 6-7 (5-7), 6-3, 6-2 |
| Semifinals | Marin Cilic | Win | 6-2, 3-6, 7-6 (12-10) |
| Final | Arthur Rinderknech | Win | 6-7 (6-8), 7-6 (7-5), 6-3 |
| Adelaide International 1 | ||
| Surface: Hard | Date: Jan. 3 - Jan. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 6-4, 6-3 |
| Second Round | Frances Tiafoe | Win | 3-6, 7-5, 6-1 |
| Quarterfinals | Mikael Ymer | Win | 7-6 (11-9), 4-6, 6-4 |
| Semifinals | Gael Monfils | Loss | 5-7, 0-6 |
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