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| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 7 - Oct. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Maximilian Marterer | Win | 6-3, 7-6 (7-5) |
| Second Round | Novak Djokovic | Loss | 3-6, 5-7 |
| Rakuten Japan Open Tennis Championships | ||
| Surface: Hard | Date: Oct. 1 - Oct. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Win | 4-6, 6-3, 6-3 |
| Second Round | Jan-Lennard Struff | Loss | 6-7 (3-7), 7-6 (7-2), 4-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andrey Rublev | Win | 6-2, 4-6, 6-4, 6-1 |
| Second Round | Kevin Anderson | Loss | 2-6, 4-6, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fernando Verdasco | Win | 6-1, 6-2 |
| Second Round | Kevin Anderson | Loss | 6-7 (6-8), 2-6 |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Loss | 1-6, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 30 - Aug. 5 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marius Copil | Loss | 4-6, 4-6 |
| BB&T Atlanta Open | ||
| Surface: Hard | Date: Jul. 23 - Jul. 29 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Win | 6-4, 6-3 |
| Second Round | Cameron Norrie | Loss | 7-5, 4-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Loss | 3-6, 6-3, 5-7, 4-6 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tim Smyczek | Win | 6-2, 6-4 |
| Second Round | Daniil Medvedev | Win | 7-6 (8-6), 6-3 |
| Quarterfinals | Frances Tiafoe | Win | 6-4, 6-4 |
| Semifinals | Novak Djokovic | Loss | 6-7 (5-7), 4-6 |
| Libema Open | ||
| Surface: Grass | Date: Jun. 11 - Jun. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Guillermo Garcia-Lopez | Win | 6-4, 6-7 (7-9), 7-6 (7-4) |
| Second Round | Adrian Mannarino | Win | 6-4, 6-4 |
| Quarterfinals | Mackenzie McDonald | Win | 6-4, 4-6, 7-6 (7-5) |
| Semifinals | Matthew Ebden | Win | 6-4, 7-5 |
| Final | Richard Gasquet | Loss | 3-6, 6-7 (5-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tomas Berdych | Win | 7-6 (7-5), 7-6 (10-8), 1-6, 5-7, 6-2 |
| Second Round | Pierre-Hugues Herbert | Loss | 6-2, 3-6, 2-6, 6-3, 7-9 |
| TEB BNP Paribas Istanbul Open | ||
| Surface: Clay | Date: Apr. 30 - May 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 7-5, 6-3 |
| Second Round | Dusan Lajovic | Win | 4-6, 7-6 (7-3), 6-2 |
| Quarterfinals | Thomas Fabbiano | Win | 6-2, 6-2 |
| Semifinals | Taro Daniel | Loss | 3-6, 6-4, 4-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Loss | 4-6, 6-7 (5-7) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Rogerio Dutra Silva | Win | 6-3, 7-6 (7-2) |
| Second Round | Richard Gasquet | Win | 7-5, 6-1 |
| Third Round | Grigor Dimitrov | Win | 6-4, 6-4 |
| Fourth Round | Milos Raonic | Loss | 3-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Julien Benneteau | Win | 6-4, 7-6 (11-9) |
| Second Round | Fabio Fognini | Win | 4-6, 7-6 (7-2), 6-4 |
| Third Round | Adrian Mannarino | Win | 7-5, 4-6, 6-1 |
| Fourth Round | Roger Federer | Loss | 5-7, 4-6 |
| Delray Beach Open | ||
| Surface: Hard | Date: Feb. 19 - Feb. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Juan Martin Del Potro | Loss | 2-6, 4-6 |
| New York Open | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefano Travaglia | Win | 4-6, 7-6 (7-1), 6-4 |
| Second Round | Adrian Menendez-Maceiras | Loss | 5-7, 6-7 (5-7) |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 5 - Feb. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Win | 4-6, 7-5, 7-5 |
| Second Round | Andrey Rublev | Loss | 2-6, 1-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tennys Sandgren | Loss | 4-6, 6-7 (2-7), 2-6 |
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