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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Juan Ignacio Londero | Win | 6-3, 6-4 |
| Third Round | Andrey Rublev | Loss | 3-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Lloyd Harris | Win | 3-6, 6-1, 6-2, 6-2 |
| Second Round | Jay Clarke | Win | 6-1, 7-6 (7-3), 6-2 |
| Third Round | Lucas Pouille | Win | 7-5, 6-2, 7-6 (7-4) |
| Fourth Round | Matteo Berrettini | Win | 6-1, 6-2, 6-2 |
| Quarterfinals | Kei Nishikori | Win | 4-6, 6-1, 6-4, 6-4 |
| Semifinals | Rafael Nadal | Win | 7-6 (7-3), 1-6, 6-3, 6-4 |
| Final | Novak Djokovic | Loss | 6-7 (5-7), 6-1, 6-7 (4-7), 6-4, 12-13 (3-7) |
| Noventi Open | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 7-6 (7-1), 6-3 |
| Second Round | Jo-Wilfried Tsonga | Win | 7-6 (7-5), 4-6, 7-5 |
| Quarterfinals | Roberto Bautista Agut | Win | 6-3, 4-6, 6-4 |
| Semifinals | Pierre-Hugues Herbert | Win | 6-3, 6-3 |
| Final | David Goffin | Win | 7-6 (7-2), 6-1 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Sonego | Win | 6-2, 6-4, 6-4 |
| Second Round | Oscar Otte | Win | 6-4, 6-3, 6-4 |
| Third Round | Casper Ruud | Win | 6-3, 6-1, 7-6 (10-8) |
| Fourth Round | Leonardo Mayer | Win | 6-2, 6-3, 6-3 |
| Quarterfinals | Stan Wawrinka | Win | 7-6 (7-4), 4-6, 7-6 (7-5), 6-4 |
| Semifinals | Rafael Nadal | Loss | 3-6, 4-6, 2-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Joao Sousa | Win | 6-4, 6-3 |
| Third Round | Borna Coric | Win | 2-6, 6-4, 7-6 (9-7) |
| Quarterfinals | Stefanos Tsitsipas | Loss | Retired |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Richard Gasquet | Win | 6-2, 6-3 |
| Third Round | Gael Monfils | Win | 6-0, 4-6, 7-6 (7-3) |
| Quarterfinals | Dominic Thiem | Loss | 6-3, 6-7 (11-13), 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Radu Albot | Win | 4-6, 7-5, 6-3 |
| Third Round | Filip Krajinovic | Win | 7-5, 6-3 |
| Fourth Round | Daniil Medvedev | Win | 6-4, 6-2 |
| Quarterfinals | Kevin Anderson | Win | 6-0, 6-4 |
| Semifinals | Denis Shapovalov | Win | 6-2, 6-4 |
| Final | John Isner | Win | 6-1, 6-4 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Peter Gojowczyk | Win | 6-1, 7-5 |
| Third Round | Stan Wawrinka | Win | 6-3, 6-4 |
| Fourth Round | Kyle Edmund | Win | 6-1, 6-4 |
| Quarterfinals | Hubert Hurkacz | Win | 6-4, 6-4 |
| Semifinals | Rafael Nadal | Win | Retired |
| Final | Dominic Thiem | Loss | 6-3, 3-6, 5-7 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 25 - Mar. 2 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Philipp Kohlschreiber | Win | 6-4, 3-6, 6-1 |
| Second Round | Fernando Verdasco | Win | 6-3, 3-6, 6-3 |
| Quarterfinals | Marton Fucsovics | Win | 7-6 (8-6), 6-4 |
| Semifinals | Borna Coric | Win | 6-2, 6-2 |
| Final | Stefanos Tsitsipas | Win | 6-4, 6-4 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Denis Istomin | Win | 6-3, 6-4, 6-4 |
| Second Round | Daniel Evans | Win | 7-6 (7-5), 7-6 (7-3), 6-3 |
| Third Round | Taylor Fritz | Win | 6-2, 7-5, 6-2 |
| Fourth Round | Stefanos Tsitsipas | Loss | 7-6 (13-11), 6-7 (3-7), 5-7, 6-7 (5-7) |
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