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| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Win | 6-1, 6-1, 6-4 |
| Second Round | Henri Laaksonen | Win | 6-4, 7-6 (7-2), 6-2 |
| Third Round | Gael Monfils | Loss | 7-6 (7-5), 6-7 (4-7), 4-6, 7-6 (8-6), 3-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 18 - Aug. 24 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Tennys Sandgren | Win | 6-2, 6-4 |
| Third Round | Miomir Kecmanovic | Win | 6-2, 6-3 |
| Quarterfinals | Andrey Rublev | Win | 6-3, 7-6 (7-4) |
| Semifinals | Hubert Hurkacz | Loss | 3-6, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Win | 2-6, 6-3, 6-2 |
| Second Round | Lucas Pouille | 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 | Pierre-Hugues Herbert | Win | 6-3, 7-5 |
| Second Round | Dominic Thiem | Loss | 4-6, 6-3, 3-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 29 |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Loss | 6-7 (0-7), 4-6, 3-6 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Juan Martin Del Potro | Loss | 5-7, 4-6 |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 10 - Jun. 16 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Loss | 5-7, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Loss | 6-7 (1-7), 3-6, 4-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 19 - May 25 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ugo Humbert | Win | 2-6, 7-6 (7-3), 6-2 |
| Quarterfinals | Benoit Paire | Loss | 3-6, 6-4, 6-7 (4-7) |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pablo Carreno Busta | Win | 6-3, 7-6 (7-5) |
| Second Round | Novak Djokovic | Loss | 1-6, 3-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Loss | 2-6, 6-7 (7-9) |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 22 - Apr. 28 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Cristian Garin | Loss | 5-7, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Loss | 7-5, 3-6, 1-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Daniel Evans | Win | 4-6, 6-1, 6-3 |
| Third Round | Andrey Rublev | Win | 6-3, 7-6 (7-5) |
| Fourth Round | Stefanos Tsitsipas | Win | 4-6, 6-3, 7-6 (7-3) |
| Quarterfinals | Frances Tiafoe | Win | 6-7 (5-7), 6-4, 6-2 |
| Semifinals | Roger Federer | Loss | 2-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 24 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Steve Johnson | Win | 6-3, 6-4 |
| Third Round | Marin Cilic | Win | 6-4, 6-2 |
| Fourth Round | Hubert Hurkacz | Loss | 6-7 (3-7), 6-2, 3-6 |
| Open 13 Provence | ||
| Surface: Hard | Date: Feb. 18 - Feb. 24 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mikhail Kukushkin | Loss | 4-6, 6-7 (4-7) |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Franko Skugor | Win | 7-5, 6-3 |
| Second Round | Tomas Berdych | Win | 6-4, 6-3 |
| Quarterfinals | Stan Wawrinka | Loss | 4-6, 6-7 (4-7) |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marcel Granollers | Win | 6-4, 7-6 (7-1) |
| Quarterfinals | Pierre-Hugues Herbert | Loss | 5-7, 6-7 (4-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 25 |
| Round | Opponent | W / L | Result |
| First Round | Pablo Andujar | Win | 6-2, 6-3, 7-6 (7-3) |
| Second Round | Taro Daniel | Win | 6-3, 7-6 (7-2), 6-3 |
| Third Round | Novak Djokovic | Loss | 3-6, 4-6, 6-4, 0-6 |
| ASB Classic | ||
| Surface: Hard | Date: Dec. 31 - Jan. 12 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Loss | 6-4, 4-6, 4-6 |
© 2019 by STATS.