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| Rolex Paris Masters | ||
| Surface: Hard | Date: Oct. 28 - Nov. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Sam Querrey | Win | 5-7, 6-3, 7-5 |
| Second Round | Daniil Medvedev | Win | 4-6, 6-2, 6-4 |
| Third Round | Cristian Garin | Loss | 7-6 (7-4), 4-6, 6-7 (6-8) |
| VTB Kremlin Cup | ||
| Surface: Hard | Date: Oct. 14 - Oct. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Jarry | Win | 6-4, 6-2 |
| Second Round | Miomir Kecmanovic | Win | 6-3, 6-4 |
| Quarterfinals | Marin Cilic | Loss | 4-6, 6-4, 6-7 (2-7) |
| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 6 - Oct. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kyle Edmund | Win | 6-4, 7-6 (7-3) |
| Second Round | Alexander Zverev | Loss | 6-7 (13-15), 6-7 (3-7) |
| China Open | ||
| Surface: Hard | Date: Sep. 28 - Oct. 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | 6-7 (7-9), 6-3, 7-6 (7-4) |
| Second Round | Karen Khachanov | Loss | 6-7 (0-7), 6-7 (5-7) |
| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Win | 3-6, 6-3, 6-7 (6-8), 6-1, 6-4 |
| Second Round | Stan Wawrinka | Loss | 4-6, 3-6, 7-6 (7-3), 3-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 18 - Aug. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Raymond Sarmiento | Win | 6-1, 7-6 (7-5) |
| Second Round | Frances Tiafoe | Loss | 2-4 Retired |
| Generali Open | ||
| Surface: Clay | Date: Jul. 29 - Aug. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Win | 7-6 (10-8), 7-5 |
| Second Round | Dusan Lajovic | Win | 3-6, 6-4, 6-3 |
| Quarterfinals | Albert Ramos-Vinolas | Loss | 3-6, 4-6 |
| Hamburg Open | ||
| Surface: Red Clay | Date: Jul. 22 - Jul. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benoit Paire | Win | 6-7 (4-7), 7-5, 6-3 |
| Second Round | Richard Gasquet | Win | 7-6 (7-5), 7-5 |
| Quarterfinals | Nikoloz Basilashvili | Loss | 2-6, 3-6 |
| SkiStar Swedish Open | ||
| Surface: Clay | Date: Jul. 15 - Jul. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pablo Carreno Busta | Win | 6-4, 4-6, 7-5 |
| Second Round | Cristian Garin | Win | 6-4, 6-4 |
| Quarterfinals | Nicolas Jarry | Loss | 1-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Martin Klizan | Win | 3-6, 6-0, 6-3, 6-4 |
| Second Round | David Goffin | Loss | 2-6, 4-6, 3-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 23 - Jun. 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Cameron Norrie | Loss | 3-6, 6-7 (4-7) |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mikhail Kukushkin | Win | 6-1, 6-3 |
| Second Round | Stefanos Tsitsipas | Loss | 6-4, 6-7 (0-7), 6-7 (4-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kyle Edmund | Loss | 6-7 (1-7), 7-5, 4-6, 6-4, 5-7 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 19 - May 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Loss | 2-6, 5-7 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Richard Gasquet | Win | 6-1, 4-6, 6-3 |
| Second Round | Rafael Nadal | Loss | 0-6, 1-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | 6-2, 4-6, 7-5 |
| Second Round | Diego Schwartzman | Win | 6-1, 6-2 |
| Third Round | Novak Djokovic | Loss | 1-6, 6-7 (2-7) |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Pablo Carreno Busta | Win | 5-7, 6-1, 6-2 |
| Second Round | Alejandro Davidovich Fokina | Loss | 1-6, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mikhail Kukushkin | Loss | 3-6, 4-6 |
| Fayez Sarofim & Co. US Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 8 - Apr. 14 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Christian Garin | Loss | 6-3, 6-7 (4-7), 6-7 (7-9) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Jarry | Win | 6-7 (1-7), 6-2, 7-6 (7-5) |
| Second Round | Gilles Simon | Win | 6-4, 6-2 |
| Third Round | Borna Coric | Loss | 7-6 (7-2), 2-6, 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marcos Giron | Loss | 6-7 (3-7), 6-7 (1-7) |
| Open 13 Provence | ||
| Surface: Hard | Date: Feb. 18 - Feb. 24 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Loss | 6-7 (12-14), 6-7 (0-7) |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniil Medvedev | Loss | 6-7 (2-7), 2-6 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Adrian Menendez-Maceiras | Win | 6-1, 6-1 |
| Second Round | Antoine Hoang | Win | 6-3, 7-5 |
| Quarterfinals | Jo-Wilfried Tsonga | Loss | 7-6 (8-6), 6-7 (4-7), 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Win | 3-6, 7-6 (8-6), 6-4, 6-7(4-7), 7-6 (10-6) |
| Second Round | Alexander Zverev | Loss | 6-7 (5-7), 4-6, 7-5, 7-6 (8-6), 1-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 6 - Jan. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Loss | 5-7, 6-2, 4-6 |
| Brisbane International presented by Suncorp | ||
| Surface: Hard | Date: Dec. 31 - Jan. 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Win | 4-6, 6-3, 6-4 |
| Second Round | Nick Kyrgios | Win | 6-7 (5-7), 6-2, 6-3 |
| Quarterfinals | Yasutaka Uchiyama | Win | 6-4, 3-6, 7-6 (7-4) |
| Semifinals | Kei Nishikori | Loss | 2-6, 2-6 |
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