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| Next Gen ATP Finals | ||
| Surface: Hard | Date: Nov. 6 - Nov. 10 | Seed: 2 |
| Round | Opponent | W / L | Result |
| Round Robin | Liam Caruana | Win | 4-1, 4-1, 4-2 4-1, 3-4 (5-7), 4-1, 4-2 4-3 (10-8), 4-1, 4-2 |
| Round Robin | Andrey Rublev | Win | 4-1, 4-1, 4-2 4-1, 3-4 (5-7), 4-1, 4-2 4-3 (10-8), 4-1, 4-2 |
| Round Robin | Taylor Fritz | Win | 4-1, 4-1, 4-2 4-1, 3-4 (5-7), 4-1, 4-2 4-3 (10-8), 4-1, 4-2 |
| Semifinals | Jaume Munar | Win | 3-4 (5-7), 4-1, 4-1, 3-4(4-7), 4-2 |
| Final | Stefanos Tsitsipas | Loss | 4-2, 1-4, 3-4 (3-7), 3-4 (3-7) |
| Rolex Paris Masters | ||
| Surface: Hard | Date: Oct. 29 - Nov. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Feliciano Lopez | Loss | 7-6 (7-4), 4-6, 6-7 (6-8) |
| Intrum Stockholm Open | ||
| Surface: Hard | Date: Oct. 15 - Oct. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Philipp Kohlschreiber | Loss | 6-7 (3-7), 7-6 (7-2), 1-6 |
| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 7 - Oct. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Vasek Pospisil | Win | 6-4, 7-6 (7-4) |
| Second Round | Benoit Paire | Win | 6-4, 6-3 |
| Third Round | Alexander Zverev | Loss | 1-6, 4-6 |
| Rakuten Japan Open Tennis Championships | ||
| Surface: Hard | Date: Oct. 1 - Oct. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gilles Simon | Win | 6-7 (1-7), 7-6 (7-5), 6-2 |
| Second Round | Stefanos Tsitsipas | Loss | 3-6, 7-5, 1-6 |
| Shenzhen Open | ||
| Surface: Hard | Date: Sep. 24 - Sep. 30 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Yuichi Sugita | Win | 6-3, 6-0 |
| Second Round | Mackenzie McDonald | Win | 1-6, 7-6 (7-1), 6-0 |
| Quarterfinals | Damir Dzumhur | Win | 6-3, 7-6 (9-7) |
| Semifinals | Pierre-Hugues Herbert | Loss | 5-7, 6-2, 6-7 (8-10) |
| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taro Daniel | Win | 6-0, 6-1, 6-2 |
| Second Round | Frances Tiafoe | Win | 6-4, 6-0, 5-7, 6-2 |
| Third Round | Marin Cilic | Loss | 6-4, 6-3, 3-6, 4-6, 5-7 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 19 - Aug. 25 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Daniil Medvedev | Loss | 3-6, 3-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 30 - Aug. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Vasek Pospisil | Win | 6-7 (6-8), 6-2, 6-3 |
| Second Round | Steve Johnson | Win | 6-4, 7-5 |
| Third Round | Hyeon Chung | Win | 6-2, 4-6, 6-2 |
| Quarterfinals | Andy Murray | Win | Retired |
| Semifinals | Andrey Rublev | Win | 5-7, 7-6 (8-6), 6-4 |
| Final | Alexander Zverev | Loss | 2-6, 4-6 |
| BB&T Atlanta Open | ||
| Surface: Hard | Date: Jul. 23 - Jul. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Win | 1-6, 7-6 (7-0), 7-6 (7-4) |
| Second Round | John Isner | Loss | 3-6, 2-6 |
| Dell Technologies Hall of Fame Open | ||
| Surface: Grass | Date: Jul. 16 - Jul. 22 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Ivo Karlovic | Loss | 7-6 (7-2), 6-7 (3-7), 5-7 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | 6-4, 6-7 (6-8), 7-6 (7-5), 6-4 |
| Second Round | Pierre-Hugues Herbert | Win | 6-2, 6-7 (8-10), 7-5, 6-3 |
| Third Round | Rafael Nadal | Loss | 1-6, 2-6, 4-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 24 - Jun. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mikhail Kukushkin | Loss | 1-6, 2-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kyle Edmund | Loss | 2-6, 4-6, 3-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 30 - May 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gastao Elias | Win | 6-3, 6-1 |
| Second Round | Kyle Edmund | Loss | 2-6, 5-7 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yoshihito Nishioka | Loss | 2-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Win | 3-6, 7-6 (7-3), 7-6 (7-5) |
| Second Round | Juan Martin Del Potro | Loss | 2-6, 1-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tomas Berdych | Loss | 3-6, 6-3, 0-6, 1-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fernando Verdasco | Win | 6-4, 6-2 |
| Second Round | Damir Dzumhur | Win | 6-2, 3-0 Retired |
| Quarterfinals | Feliciano Lopez | Win | 6-4, 6-4 |
| Semifinals | Benoit Paire | Win | 4-6, 6-1, 6-1 |
| Final | Daniil Medvedev | Loss | 6-1, 4-6, 5-7 |
| Brisbane International presented by Suncorp | ||
| Surface: Hard | Date: Dec. 31 - Jan. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Steve Johnson | Win | 7-6 (9-7), 6-4 |
| Second Round | Milos Raonic | Win | 6-4, 6-4 |
| Quarterfinals | Michael Mmoh | Win | 6-4, 6-0 |
| Semifinals | Ryan Harrison | Loss | 6-4, 6-7 (5-7), 4-6 |
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