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| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Loss | 1-6, 6-7 (2-7) |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Goffin | Win | 6-4, 7-5 |
| Second Round | Gael Monfils | Loss | 6-1, 4-6, 2-6 |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Sonego | Win | 7-5, 4-6, 7-6 (10-8) |
| Second Round | Thiago Monteiro | Win | 6-7 (1-7), 6-4, 6-3 |
| Quarterfinals | Marco Cecchinato | Loss | 6-1, 5-7, 5-7 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 22 - Apr. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Win | 6-4, 6-1 |
| Second Round | Stefanos Tsitsipas | 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 | Nikoloz Basilashvili | Win | 7-5, 3-6, 6-1 |
| Second Round | Cameron Norrie | Loss | 6-7 (3-7), 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 29 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Felix Auger-Aliassime | Loss | 4-6, 6-4, 0-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 29 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Stan Wawrinka | Loss | 4-6, 7-6 (7-5), 5-7 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 25 - Mar. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Win | 6-1, 7-6 (7-5) |
| Second Round | Jan-Lennard Struff | Win | 6-4, 6-2 |
| Quarterfinals | Roger Federer | Loss | 6-7 (6-8), 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Martin Klizan | Win | 7-6 (7-4), 6-4 |
| Second Round | Nikoloz Basilashvili | Win | 7-6 (7-1), 6-1 |
| Quarterfinals | Kei Nishikori | Loss | 3-6, 2-6 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Win | 6-2, 7-6 (7-2) |
| Second Round | Yannick Maden | Win | 7-6 (7-3), 3-6, 6-4 |
| Quarterfinals | Roberto Bautista Agut | Win | Retired |
| Semifinals | Matteo Berrettini | Win | 5-7, 7-5, 6-3 |
| Final | Daniil Medvedev | Loss | 4-6, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | 6-3, 6-4, 6-7 (5-7), 6-3 |
| Second Round | Borna Coric | Loss | 4-6, 3-6, 4-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 6 - Jan. 12 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | James Duckworth | Win | 3-6, 6-3, 6-4 |
| Second Round | John Millman | Loss | 3-6, 4-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Dec. 31 - Jan. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marius Copil | Win | 6-3, 6-2 |
| Second Round | Novak Djokovic | Loss | 6-4, 4-6, 1-6 |
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