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| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 6-3, 4-6, 6-4, 6-4 |
| Second Round | Leonardo Mayer | Win | 6-7 (4-7), 6-1, 7-6 (9-7), 6-3 |
| Third Round | Novak Djokovic | Loss | 5-7, 7-6 (7-5), 1-6, 4-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 23 - Jun. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | 6-4, 6-4 |
| Second Round | Steve Johnson | Win | 6-3, 7-6 (8-6) |
| Quarterfinals | Taylor Fritz | Loss | 4-6, 6-7 (5-7) |
| Noventi Open | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Loss | 6-7 (3-7), 1-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Novak Djokovic | Loss | 4-6, 2-6, 2-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 19 - May 25 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Pablo Cuevas | Loss | 4-6, 4-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alex De Minaur | Win | 6-3, 6-4 |
| Second Round | Lucas Pouille | Win | 7-5, 6-1 |
| Third Round | Alexander Zverev | Loss | 6-3, 4-6, 4-6 |
| Gazprom Hungarian Open | ||
| Surface: Red Clay | Date: Apr. 22 - Apr. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Attila Balazs | Loss | 3-6, 4-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Borna Coric | Loss | 4-6, 7-5, 5-7 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Win | 6-4, 6-3 |
| Second Round | Dominic Thiem | Win | 6-4, 6-4 |
| Third Round | Felix Auger-Aliassime | Loss | 6-7 (5-7), 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Donald Young | Win | 6-3, 6-3 |
| Second Round | Lucas Pouille | Win | 6-2, 3-6, 6-4 |
| Third Round | Kei Nishikori | Win | 4-6, 6-4, 6-3 |
| Fourth Round | Denis Shapovalov | Win | 7-6 (7-3), 2-6, 6-3 |
| Quarterfinals | Roger Federer | Loss | 4-6, 4-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 25 - Mar. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Corentin Moutet | Win | 6-3, 7-5 |
| Second Round | Kei Nishikori | Win | 7-5, 5-7, 6-2 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 6-7 (4-7), 7-6 (7-1), 1-6 |
| Open 13 Provence | ||
| Surface: Hard | Date: Feb. 18 - Feb. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Filip Krajinovic | Win | 6-3, 6-2 |
| Second Round | Stefanos Tsitsipas | Loss | 4-6, 2-6 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ernests Gulbis | Loss | 4-6, 6-7 (5-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ivo Karlovic | Loss | 7-6 (7-5), 6-7 (5-7), 6-7 (3-7), 6-7 (5-7) |
| Tata Open Maharashtra | ||
| Surface: Hard | Date: Dec. 31 - Jan. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ilya Ivashka | Loss | 7-6 (11-9), 2-6, 3-6 |
