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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Taylor Fritz | Win | 6-4, 4-6, 6-4 |
| Second Round | Guido Pella | Win | 6-1, 7-5 |
| Third Round | Adrian Mannarino | Win | 7-6 (8-6), 6-2 |
| Quarterfinals | Yoshihito Nishioka | Win | Retired |
| Semifinals | Richard Gasquet | Win | 6-3, 6-4 |
| Final | Daniil Medvedev | Loss | 6-7 (3-7), 4-6 |
| Coupe Rogers presentee par Banque Nationale | ||
| Surface: Hard | Date: Aug. 5 - Aug. 11 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Loss | 4-6, 6-7 (4-7) |
| Citi Open | ||
| Surface: Hard | Date: Jul. 29 - Aug. 4 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Yoshihito Nishioka | Loss | 7-6 (7-5), 2-6, 6-7 (5-7) |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bradley Klahn | Win | 6-4, 6-4, 6-4 |
| Second Round | Jeremy Chardy | Win | 6-2, 6-4, 6-3 |
| Third Round | Daniil Medvedev | Win | 4-6, 6-2, 3-6, 6-3, 7-5 |
| Fourth Round | Fernando Verdasco | Win | 7-6 (11-9), 2-6, 6-3, 6-4 |
| Quarterfinals | Novak Djokovic | Loss | 4-6, 0-6, 2-6 |
| Noventi Open | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Win | 6-1, 6-1 |
| Second Round | Radu Albot | Win | 4-6, 6-4, 6-3 |
| Quarterfinals | Alexander Zverev | Win | 3-6, 6-1, 7-6 (7-3) |
| Semifinals | Matteo Berrettini | Win | 7-6 (7-4), 6-3 |
| Final | Roger Federer | Loss | 6-7 (2-7), 1-6 |
| Libema Open | ||
| Surface: Grass | Date: Jun. 10 - Jun. 16 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Alejandro Davidovich Fokina | Win | 6-0, 6-2 |
| Second Round | Pierre-Hugues Herbert | Win | 6-3, 7-5 |
| Quarterfinals | Adrian Mannarino | Loss | 6-4, 5-7, 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 27 |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Win | 6-0, 6-2, 6-2 |
| Second Round | Miomir Kecmanovic | Win | 6-2, 6-4, 6-3 |
| Third Round | Rafael Nadal | Loss | 1-6, 3-6, 6-4, 3-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stan Wawrinka | Win | 4-6, 6-0, 6-2 |
| Second Round | Juan Martin Del Potro | Loss | 4-6, 2-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marton Fucsovics | Loss | 4-6, 5-7 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Joao Sousa | Win | 6-3, 6-2 |
| Quarterfinals | Malek Jaziri | Win | 4-6, 7-6 (7-4), 6-2 |
| Semifinals | Stefanos Tsitsipas | Loss | 6-3, 4-6, 4-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 22 - Apr. 28 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jan-Lennard Struff | Loss | 6-7 (6-8), 3-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Guido Andreozzi | Win | 6-1, 6-4 |
| Second Round | Dusan Lajovic | Loss | 3-6, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pablo Andujar | Win | 6-4, 6-1 |
| Third Round | Marco Cecchinato | Win | 6-4, 6-4 |
| Fourth Round | Frances Tiafoe | Loss | 5-7, 6-7 (6-8) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Filip Krajinovic | Loss | 3-6, 3-6 |
| Open 13 Provence | ||
| Surface: Hard | Date: Feb. 18 - Feb. 24 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Benoit Paire | Win | 6-2, 6-3 |
| Quarterfinals | Gilles Simon | Win | 6-2, 6-4 |
| Semifinals | Stefanos Tsitsipas | Loss | 6-7 (1-7), 2-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Loss | 6-7 (5-7), 5-7 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Filip Krajinovic | Loss | 4-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Christian Garin | Win | 6-0, 6-2, 6-2 |
| Second Round | Marius Copil | Win | 5-7, 7-5, 6-2, 6-4 |
| Third Round | Daniil Medvedev | Loss | 2-6, 6-7 (3-7), 3-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Dec. 31 - Jan. 5 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Loss | 6-3, 4-6, 6-7 (4-7) |
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