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| Generali Open | ||
| Surface: Clay | Date: Jul. 29 - Aug. 3 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Dennis Novak | Win | 6-7 (1-7), 6-0, 6-2 |
| Quarterfinals | Casper Ruud | Loss | 3-6, 6-7 (4-7) |
| Hamburg Open | ||
| Surface: Red Clay | Date: Jul. 22 - Jul. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dominic Thiem | Loss | 3-6, 6-7 (3-7) |
| SkiStar Swedish Open | ||
| Surface: Clay | Date: Jul. 15 - Jul. 21 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Federico Delbonis | Loss | 4-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Win | 4-6, 7-6 (10-8), 2-6, 6-4, 6-2 |
| Second Round | Jiri Vesely | Loss | 6-4, 6-7 (5-7), 4-6, 4-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 23 - Jun. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Jarry | Loss | 1-6, 6-7 (4-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Maxime Janvier | Win | 6-4, 6-4, 6-2 |
| Second Round | Kyle Edmund | Win | 7-6 (7-3), 6-3, 2-1 Retired |
| Third Round | Dominic Thiem | Loss | 3-6, 6-4, 2-6, 5-7 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 19 - May 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Win | 6-4, 6-4 |
| Second Round | Benoit Paire | Loss | 4-6, 3-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Salvatore Caruso | Win | 6-2, 6-2 |
| Second Round | Filippo Baldi | Win | 6-2, 7-5 |
| Quarterfinals | Frances Tiafoe | Win | 6-0, 6-7 (5-7), 6-2 |
| Semifinals | Alejandro Davidovich Fokina | Win | 3-6, 6-2, 6-2 |
| Final | Stefanos Tsitsipas | Loss | 3-6, 6-7 (4-7) |
| Gazprom Hungarian Open | ||
| Surface: Red Clay | Date: Apr. 22 - Apr. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yannick Maden | Win | 6-3, 3-6, 6-4 |
| Second Round | Marin Cilic | Win | 5-7, 7-6 (8-6), 7-6 (7-3) |
| Quarterfinals | Matteo Berrettini | Loss | 3-6, 6-1, 3-6 |
| Fayez Sarofim & Co. US Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 8 - Apr. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christian Garin | Loss | 6-4, 4-6, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Loss | 4-6, 7-6 (8-6), 3-6 |
| Brasil Open | ||
| Surface: Clay | Date: Feb. 25 - Mar. 3 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Loss | 7-5, 3-6, 3-6 |
| Rio Open presented by Claro HDTV | ||
| Surface: Clay | Date: Feb. 18 - Feb. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Diego Schwartzman | Win | 6-1, 4-1 Retired |
| Second Round | Juan Ignacio Londero | Win | 6-1, 6-4 |
| Quarterfinals | Albert Ramos-Vinolas | Win | 6-3, 3-6, 6-3 |
| Semifinals | Felix Auger-Aliassime | Loss | 3-6, 6-3, 3-6 |
| Argentina Open | ||
| Surface: Clay | Date: Feb. 11 - Feb. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marcelo Arevalo | Win | 6-2, 6-1 |
| Second Round | Joao Sousa | Win | 6-4, 7-5 |
| Quarterfinals | Dominic Thiem | Loss | 6-4, 4-6, 3-6 |
| Cordoba Open | ||
| Surface: Clay | Date: Feb. 4 - Feb. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Facundo Bagnis | Win | 6-4, 6-4 |
| Second Round | Malek Jaziri | Win | 7-6 (7-5), 6-2 |
| Quarterfinals | Aljaz Bedene | Win | 7-6 (7-2), 6-1 |
| Semifinals | Guido Pella | Loss | 1-6, 6-3, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 6-4, 7-5, 6-1 |
| Second Round | Grigor Dimitrov | Loss | 3-6, 7-6 (7-5), 3-6, 5-7 |
| ASB Classic | ||
| Surface: Hard | Date: Dec. 31 - Jan. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Loss | 5-7, 1-6 |
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