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| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 6 - Oct. 13 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Alex De Minaur | Win | 7-6 (7-1), 6-4 |
| Second Round | Lucas Pouille | Win | 7-5, 6-3 |
| Third Round | Novak Djokovic | Loss | 5-7, 3-6 |
| China Open | ||
| Surface: Hard | Date: Sep. 28 - Oct. 6 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Win | 6-4, 6-7 (5-7), 6-3 |
| Second Round | Daniel Evans | Win | 7-6 (7-3), 7-5 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 6-7 (3-7), 3-6 |
| Chengdu Open | ||
| Surface: Hard | Date: Sep. 23 - Sep. 29 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Egor Gerasimov | Loss | 7-6 (13-11), 6-7 (5-7), 6-7 (4-7) |
| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Guillermo Garcia-Lopez | Win | 6-3, 6-4, 6-4 |
| Second Round | Jan-Lennard Struff | Win | 6-3, 7-6 (7-4), 7-6 (7-5) |
| Third Round | Marin Cilic | Loss | 5-7, 6-3, 6-7 (6-8), 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: 13 |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 7-6 (7-3), 1-6, 7-5 |
| Second Round | Pablo Carreno Busta | Loss | 4-6, 7-6 (7-1), 6-7 (6-8) |
| Coupe Rogers presentee par Banque Nationale | ||
| Surface: Hard | Date: Aug. 5 - Aug. 11 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Jordan Thompson | Win | 3-6, 6-3, 7-6 (8-6) |
| Second Round | Cristian Garin | Loss | 3-6, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 29 - Aug. 4 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Hubert Hurkacz | Win | 6-4, 6-4 |
| Third Round | Benoit Paire | Loss | 6-7 (3-7), 3-6 |
| BB&T Atlanta Open | ||
| Surface: Hard | Date: Jul. 22 - Jul. 28 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Reilly Opelka | Loss | 6-7 (2-7), 7-6 (7-5), 6-7 (5-7) |
| Hall of Fame Open | ||
| Surface: Grass | Date: Jul. 15 - Jul. 21 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Kamil Majchrzak | Win | 6-4, 6-7 (5-7), 6-3 |
| Quarterfinals | Matthew Ebden | Win | 4-6, 6-3, 6-4 |
| Semifinals | Ugo Humbert | Win | 6-7 (4-7), 7-6 (7-5), 6-3 |
| Final | Alexander Bublik | Win | 7-6 (7-2), 6-3 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Casper Ruud | Win | 6-3, 6-4, 7-6 (11-9) |
| Second Round | Mikhail Kukushkin | Loss | 4-6, 7-6 (7-3), 6-4, 1-6, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Lorenzo Sonego | Win | 7-6 (7-2), 7-6 (9-7) |
| Third Round | Albert Ramos-Vinolas | Win | 7-5, 7-6 (8-6) |
| Fourth Round | Kyle Edmund | Win | 7-6 (7-5), 7-6 (7-3) |
| Quarterfinals | Roberto Bautista Agut | Win | 7-6 (7-1), 7-6 (7-5) |
| Semifinals | Felix Auger-Aliassime | Win | 7-6 (7-3), 7-6 (7-4) |
| Final | Roger Federer | Loss | 1-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alexei Popyrin | Win | 6-0, 6-2 |
| Third Round | Guido Pella | Win | 6-3, 6-4 |
| Fourth Round | Karen Khachanov | Loss | 4-6, 6-7 (1-7) |
| Abierto Mexicano TELCEL presentado por HSBC | ||
| Surface: Hard | Date: Feb. 25 - Mar. 3 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Adrian Mannarino | Win | 6-3, 4-6, 6-3 |
| Second Round | Sam Querrey | Win | 6-4, 6-4 |
| Quarterfinals | John Millman | Win | 7-6 (7-2), 6-7 (4-7), 7-6 (7-4) |
| Semifinals | Nick Kyrgios | Loss | 5-7, 7-5, 6-7 (7-9) |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 18 - Feb. 24 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Peter Polansky | Win | 6-3, 7-6 (7-4) |
| Second Round | Lukas Lacko | Win | 6-4, 6-3 |
| Quarterfinals | Adrian Mannarino | Win | 7-6 (7-2), 6-4 |
| Semifinals | Daniel Evans | Loss | 6-3, 2-6, 3-6 |
| New York Open | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Bernard Tomic | Win | 7-6 (9-7), 6-4 |
| Quarterfinals | Jordan Thompson | Win | 6-4, 6-1 |
| Semifinals | Reilly Opelka | Loss | 7-6 (10-8), 6-7 (14-16), 6-7 (4-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Loss | 6-7 (4-7), 6-7 (6-8), 7-6 (7-4), 6-7 (5-7) |
| ASB Classic | ||
| Surface: Hard | Date: Dec. 31 - Jan. 12 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Taylor Fritz | Loss | 6-7 (3-7), 6-7 (5-7) |
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