| ||||||||||||||
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: Sep. 14 - Sep. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Miomir Kecmanovic | Win | 6-4, 6-1 |
| Second Round | Grigor Dimitrov | Loss | 1-6, 0-6 |
| Generali Open | ||
| Surface: Clay | Date: Sep. 8 - Sep. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Loss | 3-6, 0-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 31 - Sep. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andy Murray | Loss | 6-4, 6-4, 6-7 (5-7), 6-7 (4-7), 4-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 24 - Feb. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Loss | 5-7, 2-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 17 - Feb. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 3-6, 6-4, 6-2 |
| Second Round | Noah Rubin | Win | 6-1, 6-2 |
| Quarterfinals | Brandon Nakashima | Win | 3-6, 7-6 (7-5), 6-4 |
| Semifinals | Ugo Humbert | Win | 1-6, 6-4, 6-0 |
| Final | Reilly Opelka | Loss | 5-7, 7-6 (7-4), 2-6 |
| New York Open | ||
| Surface: Hard | Date: Feb. 10 - Feb. 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Henri Laaksonen | Win | 6-3, 0-6, 6-2 |
| Second Round | Reilly Opelka | Loss | 4-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 20 - Feb. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 6-4, 3-6, 6-2, 7-6(7-1) |
| Second Round | Daniel Evans | Win | 6-4, 6-3, 6-4 |
| Third Round | Novak Djokovic | Loss | 3-6, 2-6, 2-6 |
© 2020 by STATS PERFORM.Any commercial use or distribution without the express written consent of STATS PERFORM is strictly prohibited.