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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 | Grigor Dimitrov | Win | 6-4, 6-7 (5-7), 6-3 |
| Second Round | Marin Cilic | Win | 6-2, 6-3 |
| Third Round | Kei Nishikori | Loss | 6-3, 6-7 (2-7), 3-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nick Kyrgios | Win | 7-6 (7-4), 6-4 |
| Second Round | Marin Cilic | Loss | 6-4, 3-6, 4-6 |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thiago Monteiro | Loss | 1-6, 1-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 22 - Apr. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hugo Dellien | Win | 6-3, 6-1 |
| Second Round | David Goffin | Win | 7-6 (8-6), 6-3 |
| Third Round | Stefanos Tsitsipas | Win | 6-4, 3-6, 6-2 |
| Quarterfinals | Rafael Nadal | Loss | 5-7, 5-7 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Win | 5-7, 6-3, 6-1 |
| Second Round | Grigor Dimitrov | Loss | 6-7 (2-7), 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Loss | 6-4, 3-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 6-1, 6-3 |
| Second Round | Ricardas Berankis | Win | 3-6, 6-3, 6-2 |
| Third Round | Alexander Zverev | Win | 6-3, 6-1 |
| Fourth Round | Milos Raonic | Loss | 4-6, 3-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 25 - Mar. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Milos Raonic | Win | 6-4, 5-7, 6-4 |
| Second Round | Marton Fucsovics | Loss | 4-6, 2-6 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefano Travaglia | Win | 6-4, 6-3 |
| Second Round | Stefanos Tsitsipas | Loss | 6-7 (5-7), 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Matthew Ebden | Loss | 6-1, 4-6, 3-6, 4-6 |
| Brisbane International presented by Suncorp | ||
| Surface: Hard | Date: Dec. 31 - Jan. 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jeremy Chardy | Loss | 6-4, 3-6, 4-6 |
| ASB Classic | ||
| Surface: Hard | Date: Dec. 31 - Jan. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 7-6 (7-5), 2-0 Retired |
| Second Round | Rubin Statham | Win | 6-2, 6-1 |
| Quarterfinals | Pablo Carreno Busta | Win | 7-6 (7-5), 6-7 (6-7), 7-6 (9-7) |
| Semifinals | Cameron Norrie | Loss | 5-7, 6-4, 3-6 |
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