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| Rolex Paris Masters | ||
| Surface: Hard | Date: Oct. 29 - Nov. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pablo Carreno Busta | Win | 6-2, 6-2 |
| Second Round | Borna Coric | Loss | 4-6, 4-6 |
| Swiss Indoors Basel | ||
| Surface: Hard | Date: Oct. 22 - Oct. 28 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Maximilian Marterer | Win | 6-3, 7-5 |
| Second Round | Andreas Seppi | Win | 7-6 (7-5), 6-2 |
| Quarterfinals | Stefanos Tsitsipas | Win | 6-4, 3-6, 6-3 |
| Semifinals | Roger Federer | Loss | 1-6, 4-6 |
| VTB Kremlin Cup | ||
| Surface: Hard | Date: Oct. 15 - Oct. 21 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Dusan Lajovic | Win | 6-2, 6-1 |
| Quarterfinals | Ricardas Berankis | Win | 6-2, 1-6, 6-4 |
| Semifinals | Karen Khachanov | Loss | 1-6, 7-6 (7-5), 3-6 |
| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 7 - Oct. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ze Zhang | Win | 3-6, 7-6 (9-7), 6-4 |
| Second Round | Roger Federer | Loss | 4-6, 6-4, 4-6 |
| Rakuten Japan Open Tennis Championships | ||
| Surface: Hard | Date: Oct. 1 - Oct. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Diego Schwartzman | Win | 6-4, 6-4 |
| Second Round | Martin Klizan | Win | 6-4, 6-3 |
| Quarterfinals | Milos Raonic | Win | 7-6 (7-4), 6-3 |
| Semifinals | Denis Shapovalov | Win | 6-3, 6-3 |
| Final | Kei Nishikori | Win | 6-2, 6-4 |
| St. Petersburg Open | ||
| Surface: Hard | Date: Sep. 17 - Sep. 23 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Win | 6-4, 6-1 |
| Second Round | Mikhail Kukushkin | Win | 6-3, 6-4 |
| Quarterfinals | Dominic Thiem | Loss | 2-6, 6-3, 6-7 (2-7) |
| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Evgeny Donskoy | Win | 7-5, 6-4, 6-2 |
| Second Round | Stefanos Tsitsipas | Win | 6-4, 6-3, 4-6, 6-3 |
| Third Round | Borna Coric | Loss | 3-6, 5-7, 2-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 19 - Aug. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mirza Basic | Win | 6-4, 6-4 |
| Second Round | Alex De Minaur | Win | 6-3, 6-3 |
| Third Round | Guido Andreozzi | Win | 7-5, 6-1 |
| Quarterfinals | Ryan Harrison | Win | 7-6 (7-4), 6-4 |
| Semifinals | Taro Daniel | Win | 6-1, 6-1 |
| Final | Steve Johnson | Win | 6-4, 6-4 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Borna Coric | Loss | 2-6, 3-6 |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jack Sock | Win | 6-3, 3-6, 6-3 |
| Second Round | Felix Auger-Aliassime | Win | 3-6, 6-4, 7-6 (9-7) |
| Third Round | Alexander Zverev | Loss | 3-6, 2-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 30 - Aug. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yosuke Watanuki | Win | 3-6, 7-5, 6-1 |
| Second Round | Denis Shapovalov | Loss | 6-3, 1-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Borna Coric | Win | 7-6 (8-6), 6-2, 6-2 |
| Second Round | Guillermo Garcia-Lopez | Win | 6-3, 6-4, 6-2 |
| Third Round | Adrian Mannarino | Loss | 4-6, 3-6, 6-4, 7-5, 3-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 24 - Jun. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Steve Johnson | Loss | 2-6, 4-6 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jack Sock | Win | 7-5, 6-3 |
| Second Round | Jeremy Chardy | Loss | 6-7 (6-8), 3-6 |
| Libema Open | ||
| Surface: Grass | Date: Jun. 11 - Jun. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yuki Bhambri | Win | 6-4, 6-1 |
| Second Round | Fernando Verdasco | Loss | 4-6, 1-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Lucas Pouille | Loss | 2-6, 3-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Robin Haase | Loss | 6-3, 4-6, 1-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kyle Edmund | Loss | 4-6, 0-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 30 - May 6 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Loss | 6-7 (1-7), 5-7 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marton Fucsovics | Win | 6-7 (4-7), 6-2, 7-5 |
| Second Round | Kei Nishikori | Loss | 5-7, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Win | 2-6, 6-4, 6-2 |
| Second Round | Alexander Zverev | Loss | 4-6, 6-1, 6-7 (5-7) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Steve Johnson | Win | 7-6 (7-0), 6-4 |
| Second Round | Matteo Berrettini | Win | 6-7 (6-8), 7-5, 6-4 |
| Third Round | Pablo Carreno Busta | Loss | 1-6, 5-7 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gilles Muller | Win | 6-4, 7-6 (11-9) |
| Second Round | Pierre-Hugues Herbert | Win | 3-6, 7-6 (7-2), 6-4 |
| Quarterfinals | Andreas Seppi | Loss | 6-7 (4-7), 6-4, 3-6 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 5 - Feb. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Loss | 0-6, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thanasi Kokkinakis | Win | 6-2, 6-7 (6-8), 7-6 (10-8), 6-4 |
| Second Round | Hyeon Chung | Loss | 6-7 (4-7), 1-6, 1-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 7 - Jan. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Philipp Kohlschreiber | Win | 6-2, 6-3 |
| Second Round | Jared Donaldson | Win | 6-3, 4-6, 7-5 |
| Quarterfinals | Paolo Lorenzi | Win | 6-3, 6-3 |
| Semifinals | Fabio Fognini | Win | 2-6, 6-4, 6-1 |
| Final | Alex De Minaur | Win | 1-6, 6-4, 7-5 |
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