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| Rothesay International Eastbourne | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Win | 6-3, 6-1 |
| Second Round | Daniel Evans | Win | 7-6 (7-2), 6-4 |
| Quarterfinals | Cameron Norrie | Win | 7-5, 7-5 |
| Semifinals | Jack Draper |
| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Loss | 4-6, 6-4, 4-6 |
| BOSS OPEN | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dominic Stricker | Loss | 7-6 (7-2), 6-7 (5-7), 6-7 (2-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Loss | 6-3, 6-2, 6-7 (8-10), 4-6, 4-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 2-6, 6-7 (4-7) |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Win | 6-4, 6-4 |
| Second Round | Emil Ruusuvuori | Loss | 3-6, 3-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Elias Ymer | Loss | 3-6, 0-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Loss | 4-6, 7-6 (9-7), 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Emil Ruusuvuori | Loss | 3-6, 2-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher Eubanks | Loss | 7-5, 6-7 (8-10), 4-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Loss | 7-6 (7-2), 6-7 (2-7), 6-7 (3-7) |
| Dallas Open | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Jurij Rodionov | Loss | 6-7 (3-7), 6-4, 1-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Isner | Win | 7-6 (7-2), 7-5, 6-7 (4-7), 6-7(4-7), 6-4 |
| Second Round | Tomas Machac | Win | 6-1, 3-6, 6-1, 7-6(7-5) |
| Third Round | Christopher O'Connell | Win | 6-2, 6-7 (6-8), 6-3, 6-2 |
| Fourth Round | Daniil Medvedev | Loss | 2-6, 6-7 (4-7), 7-6 (7-4), 5-7 |
| Sydney Tennis Classic | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Adrian Mannarino | Win | 6-3, 7-5 |
| Second Round | Dusan Lajovic | Win | 6-3, 6-4 |
| Quarterfinals | Daniel Evans | Loss | 4-6, 6-7 (5-7) |
| Melbourne Summer Set 1 | ||
| Surface: Hard | Date: Jan. 4 - Jan. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Rinky Hijikata | Win | 6-3, 6-0 |
| Second Round | Reilly Opelka | Win | 4-6, 7-6 (7-5), 7-6 (11-9) |
| Quarterfinals | Jaume Munar | Win | 7-6 (7-3), 6-4 |
| Semifinals | Grigor Dimitrov | Win | 7-5, 7-6 (11-9) |
| Final | Rafael Nadal | Loss | 6-7 (6-8), 3-6 |
