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| Plava Laguna Croatia Open Umag | ||
| Surface: Clay | Date: Jul. 15 - Jul. 21 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Pablo Andujar | Win | 6-1, 7-5 |
| Second Round | Jiri Vesely | Win | 3-6, 6-4, 6-4 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ernests Gulbis | Win | 6-1, 7-6 (14-12), 6-2 |
| Second Round | Hubert Hurkacz | Loss | 7-6 (7-4), 1-6, 6-7 (7-9), 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jiri Vesely | Win | 7-6 (7-3), 6-3, 6-0 |
| Second Round | Diego Schwartzman | Win | 4-6, 6-3, 6-4, 7-5 |
| Third Round | Nicolas Mahut | Win | 3-6, 7-6 (7-3), 6-4, 7-6(7-3) |
| Fourth Round | Roger Federer | Loss | 2-6, 3-6, 3-6 |
| Banque Eric Sturdza Geneva Open | ||
| Surface: Clay | Date: May 19 - May 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Loss | 2-6, 7-6 (8-6), 4-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 7-6 (7-3), 6-4 |
| Second Round | Malek Jaziri | Loss | 6-7 (2-7), 1-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 22 - Apr. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marius Copil | Win | 6-3, 6-7 (3-7), 7-5 |
| Second Round | Rafael Nadal | Loss | 7-6 (9-7), 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 | Mikael Ymer | Win | 4-6, 6-3, 6-4 |
| Second Round | Guido Pella | Win | 6-2, 6-4 |
| Third Round | Stefanos Tsitsipas | Loss | 4-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Win | 7-6 (8-6), 7-6 (7-2) |
| Second Round | Gael Monfils | Loss | 4-6, 6-3, 3-6 |
| Brasil Open | ||
| Surface: Clay | Date: Feb. 25 - Mar. 3 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Lorenzo Sonego | Win | 6-1, 3-6, 6-3 |
| Quarterfinals | Christian Garin | Loss | 6-4, 4-6, 4-6 |
| Rio Open presented by Claro HDTV | ||
| Surface: Clay | Date: Feb. 18 - Feb. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jaume Munar | Loss | 6-7 (5-7), 4-6 |
| Argentina Open | ||
| Surface: Clay | Date: Feb. 11 - Feb. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 6-3, 7-6 (7-3) |
| Second Round | Guido Pella | Loss | 4-6, 6-1, 6-7 (5-7) |
| Cordoba Open | ||
| Surface: Clay | Date: Feb. 4 - Feb. 10 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Federico Delbonis | Loss | 4-6, 7-6 (7-5), 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Jarry | Win | 7-6 (7-4), 7-6 (7-3), 4-6, 6-3 |
| Second Round | Fabio Fognini | Loss | 6-7 (3-7), 3-6, 6-7 (5-7) |
| Brisbane International presented by Suncorp | ||
| Surface: Hard | Date: Dec. 31 - Jan. 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Miomir Kecmanovic | Loss | 3-6, 1-6 |
| ASB Classic | ||
| Surface: Hard | Date: Dec. 31 - Jan. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Steve Johnson | Win | 7-5, 6-3 |
| Second Round | Matteo Berrettini | Win | 5-7, 7-6 (7-5), 6-3 |
| Quarterfinals | Tennys Sandgren | Loss | 3-6, 6-7 (5-7) |
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