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| Nitto ATP Finals | ||
| Surface: Hard | Date: Nov. 11 - Nov. 18 | Seed: 5 |
| Round | Opponent | W / L | Result |
| Round Robin | Alexander Zverev | Loss | 6-7 (5-7), 6-7 (1-7) 6-7 (2-7), 6-3, 6-4 6-7 (7-9), 2-6 |
| Round Robin | John Isner | Win | 6-7 (5-7), 6-7 (1-7) 6-7 (2-7), 6-3, 6-4 6-7 (7-9), 2-6 |
| Round Robin | Novak Djokovic | Loss | 6-7 (5-7), 6-7 (1-7) 6-7 (2-7), 6-3, 6-4 6-7 (7-9), 2-6 |
| Rolex Paris Masters | ||
| Surface: Hard | Date: Oct. 29 - Nov. 4 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Philipp Kohlschreiber | Win | 6-3, 6-4 |
| Third Round | Grigor Dimitrov | Win | 7-6 (7-5), 6-4 |
| Quarterfinals | Novak Djokovic | Loss | 6-4, 2-6, 3-6 |
| Swiss Indoors Basel | ||
| Surface: Hard | Date: Oct. 22 - Oct. 28 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Win | 6-4, 6-2 |
| Second Round | Marius Copil | Loss | 5-7, 6-7 (2-7) |
| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 7 - Oct. 14 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Nicolas Jarry | Loss | 6-2, 6-7 (6-8), 5-7 |
| Rakuten Japan Open Tennis Championships | ||
| Surface: Hard | Date: Oct. 1 - Oct. 7 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Loss | 6-3, 4-6, 6-7 (1-7) |
| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Marius Copil | Win | 7-5, 6-1, 1-1 Retired |
| Second Round | Hubert Hurkacz | Win | 6-2, 6-0, 6-0 |
| Third Round | Alex De Minaur | Win | 4-6, 3-6, 6-3, 6-4, 7-5 |
| Fourth Round | David Goffin | Win | 7-6 (8-6), 6-2, 6-4 |
| Quarterfinals | Kei Nishikori | Loss | 6-2, 4-6, 6-7 (5-7), 6-4, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marius Copil | Win | 6-7 (4-7), 6-4, 6-4 |
| Third Round | Karen Khachanov | Win | 7-6 (7-5), 3-6, 6-4 |
| Quarterfinals | Pablo Carreno Busta | Win | 7-6 (9-7), 6-4 |
| Semifinals | Novak Djokovic | Loss | 4-6, 6-3, 3-6 |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Borna Coric | Win | 6-3, 3-6, 6-1 |
| Third Round | Diego Schwartzman | Win | 6-3, 6-2 |
| Quarterfinals | Rafael Nadal | Loss | 6-2, 4-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Yoshihito Nishioka | Win | 6-1, 6-4, 6-4 |
| Second Round | Guido Pella | Loss | 6-3, 6-1, 4-6, 6-7 (3-7), 5-7 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Fernando Verdasco | Win | 6-3, 6-4 |
| Second Round | Gilles Muller | Win | 4-6, 6-3, 6-3 |
| Quarterfinals | Sam Querrey | Win | 7-6 (7-3), 6-2 |
| Semifinals | Nick Kyrgios | Win | 7-6 (7-3), 7-6 (7-4) |
| Final | Novak Djokovic | Win | 5-7, 7-6 (7-4), 6-3 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | James Duckworth | Win | 6-3, 7-5, 7-6 (7-4) |
| Second Round | Hubert Hurkacz | Win | 6-2, 6-2, 6-7 (3-7), 7-5 |
| Third Round | Steve Johnson | Win | 6-3, 6-2, 6-4 |
| Fourth Round | Fabio Fognini | Win | 6-4, 6-1, 3-6, 6-7(4-7), 6-3 |
| Quarterfinals | Juan Martin Del Potro | Loss | 6-7 (5-7), 7-5, 3-6, 5-7 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ryan Harrison | Win | 6-7 (3-7), 6-1, 7-6 (7-1) |
| Third Round | Benoit Paire | Win | 6-3, 6-4 |
| Quarterfinals | Pablo Carreno Busta | Win | 6-3, 6-3 |
| Semifinals | Alexander Zverev | Loss | 6-7 (13-15), 5-7 |
| TEB BNP Paribas Istanbul Open | ||
| Surface: Clay | Date: Apr. 30 - May 6 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Malek Jaziri | Loss | 4-6, 2-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Fernando Verdasco | Win | 6-3, 7-6 (7-4) |
| Third Round | Milos Raonic | Win | Retired |
| Quarterfinals | Kei Nishikori | Loss | 4-6, 7-6 (7-1), 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pierre-Hugues Herbert | Win | 7-5, 6-3 |
| Third Round | Vasek Pospisil | Win | 7-5, 7-6 (7-4) |
| Fourth Round | John Isner | Loss | 6-7 (0-7), 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marton Fucsovics | Win | 7-5, 6-3 |
| Third Round | Philipp Kohlschreiber | Loss | 4-6, 4-6 |
| Rio Open presented by Claro HDTV | ||
| Surface: Clay | Date: Feb. 19 - Feb. 25 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Carlos Berlocq | Win | 6-3, 6-2 |
| Second Round | Gael Monfils | Loss | 3-6, 6-7 (8-10) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Vasek Pospisil | Win | 6-2, 6-2, 4-6, 7-6(7-5) |
| Second Round | Joao Sousa | Win | 6-1, 7-5, 6-2 |
| Third Round | Ryan Harrison | Win | 7-6 (7-4), 6-3, 7-6 (7-4) |
| Fourth Round | Pablo Carreno Busta | Win | 6-7 (2-7), 6-3, 7-6 (7-0), 7-6(7-3) |
| Quarterfinals | Rafael Nadal | Win | 3-6, 6-3, 6-7 (5-7), 6-2, 2-0 Retired |
| Semifinals | Kyle Edmund | Win | 6-2, 7-6 (7-4), 6-2 |
| Final | Roger Federer | Loss | 2-6, 7-6 (7-5), 3-6, 6-3, 1-6 |
| Tata Open Maharashtra | ||
| Surface: Hard | Date: Jan. 1 - Jan. 6 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ramkumar Ramanathan | Win | 6-4, 6-3 |
| Quarterfinals | Pierre-Hugues Herbert | Win | 6-3, 6-2 |
| Semifinals | Gilles Simon | Loss | 6-1, 3-6, 2-6 |
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