| ||||||||||||||
| St. Petersburg Open | ||
| Surface: Hard | Date: Sep. 16 - Sep. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Casper Ruud | Loss | 7-6 (7-3), 4-6, 2-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Santiago Giraldo | Win | 2-6, 6-0, 7-5, 3-6, 6-4 |
| Second Round | Thomas Fabbiano | Win | 6-7 (3-7), 5-7, 6-4, 6-3, 6-3 |
| Third Round | Pablo Andujar | Loss | 4-6, 3-6, 2-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 18 - Aug. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Loss | 6-7 (3-7), 0-1 Retired |
| Citi Open | ||
| Surface: Hard | Date: Jul. 29 - Aug. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Bradley Klahn | Win | 7-6 (7-5), 6-3 |
| Second Round | Frances Tiafoe | Loss | 1-6, 6-7 (5-7) |
| BB&T Atlanta Open | ||
| Surface: Hard | Date: Jul. 22 - Jul. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Loss | 3-6, 6-7 (1-7) |
| Hall of Fame Open | ||
| Surface: Grass | Date: Jul. 15 - Jul. 21 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Alex Bolt | Win | 6-4, 2-6, 7-6 (7-4) |
| Second Round | Viktor Troicki | Win | 3-6, 6-3, 6-3 |
| Quarterfinals | Tennys Sandgren | Win | 0-6, 6-3, 6-0 |
| Semifinals | Marcel Granollers | Win | 7-6 (7-5), 3-6, 6-4 |
| Final | John Isner | Loss | 6-7 (2-7), 3-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gregoire Barrere | Loss | 6-3, 4-6, 3-6, 3-6 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Diego Schwartzman | Loss | 2-6, 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Rudolf Molleker | Win | 7-5, 6-7 (4-7), 6-1, 7-6(7-2) |
| Second Round | Dominic Thiem | Loss | 3-6, 7-6 (8-6), 3-6, 5-7 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tennys Sandgren | Win | 5-7, 6-4, 7-6 (7-5) |
| Second Round | Nick Kyrgios | Loss | 5-7, 3-6 |
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