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| Nitto ATP Finals | ||
| Surface: Hard | Date: Nov. 13 - Nov. 20 | Seed: 6 |
| Round | Opponent | W / L | Result |
| Round Robin | Daniil Medvedev | Win | 6-7 (7-9), 6-3, 7-6 (9-7) 4-6, 1-6 3-6, 6-3, 6-2 |
| Round Robin | Novak Djokovic | Loss | 6-7 (7-9), 6-3, 7-6 (9-7) 4-6, 1-6 3-6, 6-3, 6-2 |
| Round Robin | Stefanos Tsitsipas | Win | 6-7 (7-9), 6-3, 7-6 (9-7) 4-6, 1-6 3-6, 6-3, 6-2 |
| Semifinals | Casper Ruud | Loss | 2-6, 4-6 |
| Rolex Paris Masters | ||
| Surface: Hard | Date: Oct. 31 - Nov. 6 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | John Isner | Win | 6-2, 6-3 |
| Third Round | Holger Rune | Loss | 4-6, 5-7 |
| Erste Bank Open 500 | ||
| Surface: Hard | Date: Oct. 24 - Oct. 30 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Diego Schwartzman | Win | 6-4, 6-1 |
| Second Round | Grigor Dimitrov | Loss | 3-6, 4-6 |
| Gijon Open | ||
| Surface: Hard | Date: Oct. 10 - Oct. 16 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ilya Ivashka | Win | 6-3, 5-7, 6-4 |
| Quarterfinals | Tommy Paul | Win | 7-5, 6-3 |
| Semifinals | Dominic Thiem | Win | 6-4, 6-4 |
| Final | Sebastian Korda | Win | 6-2, 6-3 |
| The Astana Open | ||
| Surface: Hard | Date: Oct. 3 - Oct. 9 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 6-4, 6-3 |
| Second Round | Zhizhen Zhang | Win | 6-3, 6-2 |
| Quarterfinals | Adrian Mannarino | Win | 6-1, 6-2 |
| Semifinals | Stefanos Tsitsipas | Loss | 6-4, 4-6, 3-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 29 - Sep. 11 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Win | 7-6 (7-5), 6-3, 3-6, 4-6, 6-4 |
| Second Round | Soon Woo Kwon | Win | 6-3, 6-0, 6-4 |
| Third Round | Denis Shapovalov | Win | 6-4, 2-6, 6-7 (3-7), 6-4, 7-6 (9-7) |
| Fourth Round | Cameron Norrie | Win | 6-4, 6-4, 6-4 |
| Quarterfinals | Frances Tiafoe | Loss | 6-7 (3-7), 6-7 (0-7), 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Fabio Fognini | Win | |
| Third Round | Taylor Fritz | Loss |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 8 - Aug. 14 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Daniel Evans | Loss |
| Citi Open | ||
| Surface: Hard | Date: Aug. 1 - Aug. 7 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jack Draper | Win | |
| Third Round | Maxime Cressy | Win | |
| Quarterfinals | J.J. Wolf | Win | |
| Semifinals | Yoshihito Nishioka | Loss |
| Hamburg European Open | ||
| Surface: Red Clay | Date: Jul. 17 - Jul. 24 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Win | |
| Second Round | Francisco Cerundolo | Loss |
| Nordea Open | ||
| Surface: Clay | Date: Jul. 11 - Jul. 17 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Federico Coria | Win | |
| Quarterfinals | Laslo Djere | Win | |
| Semifinals | Sebastian Baez | Loss |
| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Loss |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Soon Woo Kwon | Win | |
| Second Round | Federico Delbonis | Win | |
| Third Round | Cristian Garin | Win | |
| Fourth Round | Jannik Sinner | Win | |
| Quarterfinals | Marin Cilic | Loss |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Filip Krajinovic | Loss |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jack Draper | Win | |
| Third Round | Daniel Evans | Win | |
| Quarterfinals | Stefanos Tsitsipas | Loss |
| Serbia Open | ||
| Surface: Red Clay | Date: Apr. 18 - Apr. 24 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jiri Lehecka | Win | |
| Quarterfinals | Taro Daniel | Win | |
| Semifinals | Fabio Fognini | Win | |
| Final | Novak Djokovic | Win |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alex De Minaur | Win | |
| Third Round | Jannik Sinner | Loss |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Nick Kyrgios | Loss |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Dominik Koepfer | Win | |
| Third Round | Frances Tiafoe | Win | |
| Fourth Round | Hubert Hurkacz | Win | |
| Quarterfinals | Grigor Dimitrov | Win | |
| Semifinals | Taylor Fritz | Loss |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Win | |
| Second Round | Soon Woo Kwon | Win | |
| Quarterfinals | Mackenzie McDonald | Win | |
| Semifinals | Hubert Hurkacz | Win | |
| Final | Jiri Vesely | Win |
| Open 13 Provence | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Richard Gasquet | Win | |
| Quarterfinals | Lucas Pouille | Win | |
| Semifinals | Benjamin Bonzi | Win | |
| Final | Felix Auger-Aliassime | Win |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Henri Laaksonen | Win | |
| Second Round | Soon Woo Kwon | Win | |
| Quarterfinals | Marton Fucsovics | Win | |
| Semifinals | Felix Auger-Aliassime | Loss |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Gianluca Mager | Win | |
| Second Round | Ricardas Berankis | Win | |
| Third Round | Marin Cilic | Loss |
