| ||||||||||||||
| Nitto ATP Finals | ||
| Surface: Hard | Date: Nov. 15 - Nov. 22 | Seed: 1 |
| Round | Opponent | W / L | Result |
| Round Robin | Diego Schwartzman | 6-3, 6-2 |
| Erste Bank Open 500 | ||
| Surface: Hard | Date: Oct. 26 - Nov. 1 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Filip Krajinovic | Win | 7-6 (8-6), 6-3 |
| Second Round | Borna Coric | Win | 7-6 (13-11), 6-3 |
| Quarterfinals | Lorenzo Sonego | Loss | 2-6, 1-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: Sep. 27 - Oct. 11 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Mikael Ymer | Win | 6-0, 6-2, 6-3 |
| Second Round | Ricardas Berankis | Win | 6-1, 6-2, 6-2 |
| Third Round | Daniel Elahi Galan | Win | 6-0, 6-3, 6-2 |
| Fourth Round | Karen Khachanov | Win | 6-4, 6-3, 6-3 |
| Quarterfinals | Pablo Carreno Busta | Win | 4-6, 6-2, 6-3, 6-4 |
| Semifinals | Stefanos Tsitsipas | Win | 6-3, 6-2, 5-7, 4-6, 6-1 |
| Final | Rafael Nadal | Loss | 0-6, 2-6, 5-7 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: Sep. 14 - Sep. 21 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Salvatore Caruso | Win | 6-3, 6-2 |
| Third Round | Filip Krajinovic | Win | 7-6 (9-7), 6-3 |
| Quarterfinals | Dominik Koepfer | Win | 6-3, 4-6, 6-3 |
| Semifinals | Casper Ruud | Win | 7-5, 6-3 |
| Final | Diego Schwartzman | Win | 7-5, 6-3 |
| US Open | ||
| Surface: Hard | Date: Aug. 31 - Sep. 13 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Damir Dzumhur | Win | 6-1, 6-4, 6-1 |
| Second Round | Kyle Edmund | Win | 6-7 (5-7), 6-3, 6-4, 6-2 |
| Third Round | Jan-Lennard Struff | Win | 6-3, 6-3, 6-1 |
| Fourth Round | Pablo Carreno Busta | Loss | 5-6 Retired |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 29 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ricardas Berankis | Win | 7-6 (7-2), 6-4 |
| Third Round | Tennys Sandgren | Win | 6-2, 6-4 |
| Quarterfinals | Jan-Lennard Struff | Win | 6-3, 6-1 |
| Semifinals | Roberto Bautista Agut | Win | 4-6, 6-4, 7-6 (7-0) |
| Final | Milos Raonic | Win | 1-6, 6-3, 6-4 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 24 - Feb. 29 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Malek Jaziri | Win | 6-1, 6-2 |
| Second Round | Philipp Kohlschreiber | Win | 6-3, 6-1 |
| Quarterfinals | Karen Khachanov | Win | 6-2, 6-2 |
| Semifinals | Gael Monfils | Win | 2-6, 7-6 (10-8), 6-1 |
| Final | Stefanos Tsitsipas | Win | 6-3, 6-4 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 20 - Feb. 2 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Win | 7-6 (7-5), 6-2, 2-6, 6-1 |
| Second Round | Tatsuma Ito | Win | 6-1, 6-4, 6-2 |
| Third Round | Yoshihito Nishioka | Win | 6-3, 6-2, 6-2 |
| Fourth Round | Diego Schwartzman | Win | 6-3, 6-4, 6-4 |
| Quarterfinals | Milos Raonic | Win | 6-4, 6-3, 7-6 (7-1) |
| Semifinals | Roger Federer | Win | 7-6 (7-1), 6-4, 6-3 |
| Final | Dominic Thiem | Win | 6-4, 4-6, 2-6, 6-3, 6-4 |
