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| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: 23 |
| Round | Opponent | W / L | Result |
| First Round | Jannik Sinner | Win | 6-3, 7-6 (7-4), 4-6, 6-3 |
| Second Round | Jeremy Chardy | Win | 6-4, 6-3, 6-7 (3-7), 6-3 |
| Third Round | Paolo Lorenzi | Win | 6-4, 7-6 (11-9), 7-6 (7-4) |
| Fourth Round | Novak Djokovic | Win | 6-4, 7-5, 2-1 Retired |
| Quarterfinals | Daniil Medvedev | Loss | 6-7 (6-8), 3-6, 6-3, 1-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Win | 5-7, 6-4, 7-6 (7-4) |
| Second Round | Andrey Rublev | Loss | 4-6, 4-6 |
| Coupe Rogers presentee par Banque Nationale | ||
| Surface: Hard | Date: Aug. 5 - Aug. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Win | 6-4, 6-4 |
| Second Round | Karen Khachanov | Loss | 4-6, 7-6 (7-3), 2-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Ruben Bemelmans | Win | 6-3, 6-2, 6-2 |
| Second Round | Reilly Opelka | Loss | 5-7, 6-3, 6-4, 4-6, 6-8 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Win | 6-3, 6-4 |
| Second Round | Nicolas Mahut | Loss | 6-3, 5-7, 6-7 (2-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 24 |
| Round | Opponent | W / L | Result |
| First Round | Jozef Kovalik | Win | 6-1, 6-7 (3-7), 6-2, 6-3 |
| Second Round | Cristian Garin | Win | 6-1, 6-4, 6-0 |
| Third Round | Grigor Dimitrov | Win | 7-6 (7-5), 7-6 (7-4), 7-6 (10-8) |
| Fourth Round | Stefanos Tsitsipas | Win | 7-6 (8-6), 5-7, 6-4, 3-6, 8-6 |
| Quarterfinals | Roger Federer | Loss | 6-7 (4-7), 6-4, 6-7 (5-7), 4-6 |
| Banque Eric Sturdza Geneva Open | ||
| Surface: Clay | Date: May 19 - May 25 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Damir Dzumhur | Loss | 6-3, 3-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Goffin | Loss | 6-4, 0-6, 2-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Win | 6-2, 6-3 |
| Second Round | Guido Pella | Win | 6-3, 6-4 |
| Third Round | Kei Nishikori | Win | 6-3, 7-6 (7-3) |
| Quarterfinals | Rafael Nadal | Loss | 1-6, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lucas Pouille | Win | 7-5, 6-3 |
| Second Round | Marco Cecchinato | Loss | 6-0, 5-7, 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Filip Krajinovic | Loss | 7-5, 2-6, 6-7 (5-7) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Win | 6-7 (4-7), 6-3, 6-3 |
| Second Round | Marton Fucsovics | Win | 6-4, 6-7 (5-7), 7-5 |
| Third Round | Roger Federer | Loss | 3-6, 4-6 |
| Abierto Mexicano TELCEL presentado por HSBC | ||
| Surface: Hard | Date: Feb. 25 - Mar. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ryan Harrison | Win | 6-4, 7-6 (8-6) |
| Second Round | Steve Johnson | Win | 7-6 (7-5), 6-4 |
| Quarterfinals | Nick Kyrgios | Loss | 5-7, 7-6 (7-3), 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benoit Paire | Win | 7-6 (7-4), 6-1 |
| Second Round | Milos Raonic | Win | 6-4, 7-6 (7-4) |
| Quarterfinals | Denis Shapovalov | Win | 6-4, 7-6 (7-4) |
| Semifinals | Kei Nishikori | Win | 6-2, 4-6, 6-4 |
| Final | Gael Monfils | Loss | 3-6, 6-1, 2-6 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marius Copil | Loss | 6-3, 6-7 (5-7), 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ernests Gulbis | Win | 3-6, 3-1 Retired |
| Second Round | Milos Raonic | Loss | 7-6 (7-4), 6-7 (6-8), 6-7 (11-13), 6-7 (5-7) |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Dec. 31 - Jan. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Karen Khachanov | Win | 7-6 (9-7), 6-4 |
| Second Round | Nicolas Jarry | Win | 6-4, 7-6 (7-3) |
| Quarterfinals | Roberto Bautista Agut | Loss | 4-6, 4-6 |
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