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| MercedesCup | ||
| Surface: Grass | Date: Jun. 11 - Jun. 17 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Denis Istomin | Loss | 6-7 (2-7), 6-7 (3-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Borna Coric | Loss | 3-6, 6-3, 3-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Win | 7-5, 6-7 (7-9), 7-6 (8-6) |
| Second Round | Jack Sock | Win | 6-4, 6-3 |
| Third Round | Kei Nishikori | Loss | 1-6, 2-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yuichi Sugita | Win | 6-4, 6-3 |
| Second Round | Roberto Bautista Agut | Win | 6-3, 4-6, 7-5 |
| Third Round | Kevin Anderson | Loss | 3-6, 6-7 (7-9) |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 30 - May 6 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Ivo Karlovic | Win | 7-5, 6-4 |
| Second Round | Mischa Zverev | Win | 6-2, 6-2 |
| Quarterfinals | Roberto Bautista Agut | Win | 6-4, 6-4 |
| Semifinals | Maximilian Marterer | Win | 6-2, 6-4 |
| Final | Alexander Zverev | Loss | 3-6, 3-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tennys Sandgren | Win | 6-2, 6-2 |
| Second Round | Albert Ramos-Vinolas | Win | 6-4, 6-2 |
| Third Round | Grigor Dimitrov | Loss | 6-4, 3-6, 4-6 |
| Grand Prix Hassan II | ||
| Surface: Red Clay | Date: Apr. 9 - Apr. 15 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Lamine Ouahab | Loss | 6-2, 0-6, 6-7 (3-7) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: 31 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Tim Smyczek | Win | 1-6, 6-4, 6-4 |
| Third Round | Marin Cilic | Win | 6-4, 6-4 |
| Fourth Round | Pierre-Hugues Herbert | Win | 6-4, 7-6 (7-1) |
| Quarterfinals | Juan Martin Del Potro | Loss | 6-3, 3-6, 4-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 26 - Mar. 3 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Gleb Sakharov | Win | 6-4, 6-2 |
| Second Round | Stefanos Tsitsipas | Loss | 6-4, 3-6, 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Win | 3-6, 7-6 (7-1), 7-6 (7-5) |
| Second Round | Roger Federer | Loss | 6-7 (8-10), 5-7 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 5 - Feb. 11 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mirza Basic | Loss | 5-7, 6-7 (5-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: 27 |
| Round | Opponent | W / L | Result |
| First Round | Yoshihito Nishioka | Loss | 3-6, 6-2, 0-6, 6-1, 2-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Daniil Medvedev | Loss | 2-6, 3-6 |
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