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| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Brandon Nakashima | Win | 6-3, 6-4 |
| Second Round | Stefanos Tsitsipas | Loss | 3-6, 7-5, 6-7 (4-7) |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Maxime Cressy | Win | 6-2, 7-6 (7-4) |
| Second Round | Diego Schwartzman | Win | 6-0, 6-3 |
| Third Round | Stefanos Tsitsipas | Loss | 3-6, 4-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Federico Coria | Win | 4-6, 6-3, 6-4 |
| Third Round | Stefanos Tsitsipas | Loss | 1-6, 4-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 6-3, 2-0 Retired |
| Second Round | Dusan Lajovic | Win | 4-6, 6-3, 6-2 |
| Third Round | Casper Ruud | Win | 6-3, 7-5 |
| Quarterfinals | Hubert Hurkacz | Win | 6-4, 3-6, 7-6 (7-2) |
| Semifinals | Alejandro Davidovich Fokina | Loss | 4-6, 7-6 (7-2), 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mackenzie McDonald | Loss | 1-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 33 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jordan Thompson | Win | 7-6 (7-3), 6-2 |
| Third Round | Alexander Bublik | Win | 6-3, 6-4 |
| Fourth Round | John Isner | Win | 6-3, 7-6 (8-6) |
| Quarterfinals | Andrey Rublev | Loss | 5-7, 2-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefan Kozlov | Loss | 6-7 (8-10), 7-5, 3-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mitchell Krueger | Win | 7-6 (7-4), 6-3 |
| Quarterfinals | John Millman | Loss | 4-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Jiri Lehecka | Win | 6-4, 4-6, 6-3, 7-5 |
| Second Round | Benoit Paire | Loss | 4-6, 4-6, 7-6 (7-4), 6-7 (2-7) |
| Melbourne Summer Set 1 | ||
| Surface: Hard | Date: Jan. 4 - Jan. 9 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Facundo Bagnis | Win | 5-7, 7-6 (7-3), 6-3 |
| Quarterfinals | Botic van de Zandschulp | Win | 6-7 (5-7), 6-0, 7-5 |
| Semifinals | Maxime Cressy | Loss | 5-7, 6-7 (9-11) |
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