| ||||||||||||||
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Frances Tiafoe | Loss | 6-7 (7-9), 3-6 |
| Coupe Rogers presentee par Banque Nationale | ||
| Surface: Hard | Date: Aug. 5 - Aug. 11 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Peter Polansky | Win | 6-7 (4-7), 6-3, 6-3 |
| Second Round | Ilya Ivashka | Win | 6-3, 7-6 (8-6) |
| Third Round | Hubert Hurkacz | Win | 6-4, 6-0 |
| Quarterfinals | Roberto Bautista Agut | Win | 6-4, 3-6, 7-6 (7-2) |
| Semifinals | Rafael Nadal | Loss | Retired |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Loss | 7-6 (8-6), 6-3, 4-6, 5-7, 0-3 Retired |
| Noventi Open | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Loss | 6-7 (6-8), 4-6 |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 10 - Jun. 16 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Steve Johnson | Win | 7-5, 5-7, 7-6 (8-6) |
| Second Round | Denis Kudla | Loss | 5-7, 7-6 (7-3), 6-7 (3-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Taro Daniel | Win | 6-0, 6-4, 6-1 |
| Second Round | Adrian Mannarino | Win | 6-3, 6-4, 6-4 |
| Third Round | Antoine Hoang | Win | 6-3, 6-2, 6-3 |
| Fourth Round | Dominic Thiem | Loss | 4-6, 4-6, 2-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Loss | 3-6, 1-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Win | 6-3, 6-1 |
| Second Round | Marton Fucsovics | Win | 1-6, 6-4, 6-2 |
| Third Round | Roger Federer | Loss | 0-6, 6-4, 6-7 (3-7) |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Reilly Opelka | Win | 3-6, 6-3, 6-0 |
| Quarterfinals | Alejandro Davidovich Fokina | Loss | 7-6 (7-2), 5-7, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Leonardo Mayer | Win | 6-4, 3-6, 6-3 |
| Third Round | Albert Ramos-Vinolas | Win | 6-0, 6-3 |
| Fourth Round | Philipp Kohlschreiber | Win | 6-0, 6-2 |
| Quarterfinals | Dominic Thiem | Loss | Retired |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 25 - Mar. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marin Cilic | Win | 6-3, 4-6, 6-0 |
| Second Round | Marcos Baghdatis | Win | 6-3, 6-2 |
| Quarterfinals | Ricardas Berankis | Win | 6-1, 6-7 (3-7), 6-2 |
| Semifinals | Stefanos Tsitsipas | Loss | 6-4, 6-7 (4-7), 6-7 (4-7) |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Goffin | Win | 7-6 (7-5), 7-5 |
| Second Round | Andreas Seppi | Win | 4-6, 6-1, 6-3 |
| Quarterfinals | Damir Dzumhur | Win | 6-1, 6-2 |
| Semifinals | Daniil Medvedev | Win | 4-6, 6-3, 6-4 |
| Final | Stan Wawrinka | Win | 6-3, 1-6, 6-2 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Viktor Troicki | Win | 6-3, 6-4 |
| Second Round | Mikhail Kukushkin | Win | 7-5, 6-3 |
| Quarterfinals | Stefanos Tsitsipas | Win | 6-3, 7-6 (7-5) |
| Semifinals | Daniil Medvedev | Loss | 2-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Win | 6-0, 6-4, 6-0 |
| Second Round | Taylor Fritz | Loss | 3-6, 7-6 (10-8), 6-7 (6-8), 6-7 (5-7) |
© 2019 by STATS.Any commercial use or distribution without the express written consent of STATS is strictly prohibited.