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| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Matthew Ebden | Win | 3-6, 6-3, 6-2 |
| Quarterfinals | Marton Fucsovics | Loss | Retired |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Andy Murray | Win | 6-4, 6-4, 6-7 (5-7), 6-7(4-7), 6-2 |
| Second Round | John Millman | Win | 6-3, 6-1, 3-6, 6-7(6-8), 6-4 |
| Third Round | Karen Khachanov | Win | 6-4, 7-5, 6-4 |
| Fourth Round | Marin Cilic | Win | 6-7 (6-8), 6-3, 6-2, 4-6, 6-4 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 5-7, 6-4, 4-6, 6-7 (2-7) |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Dec. 31 - Jan. 5 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Win | 6-1, 6-4 |
| Second Round | Guillermo Garcia-Lopez | Win | 6-1, 6-4 |
| Quarterfinals | Stan Wawrinka | Win | 6-4, 6-4 |
| Semifinals | Novak Djokovic | Win | 3-6, 7-6 (7-6), 6-4 |
| Final | Tomas Berdych | Win | 6-4, 3-6, 6-3 |
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