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| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 7 - Oct. 14 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mikhail Kukushkin | Win | 6-3, 6-2 |
| Third Round | Stefanos Tsitsipas | Win | 6-4, 7-6 (7-1) |
| Quarterfinals | Novak Djokovic | Loss | 6-7 (1-7), 3-6 |
| Rakuten Japan Open Tennis Championships | ||
| Surface: Hard | Date: Oct. 1 - Oct. 7 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Matthew Ebden | Win | 4-6, 7-6 (7-1), 6-2 |
| Second Round | Frances Tiafoe | Win | 6-3, 3-6, 6-2 |
| Quarterfinals | Richard Gasquet | Loss | 6-7 (6-8), 6-7 (4-7) |
| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Ryan Harrison | Win | 7-6 (7-4), 5-7, 4-6, 6-3, 6-4 |
| Second Round | Jeremy Chardy | Win | 6-2, 6-4, 6-4 |
| Third Round | Denis Shapovalov | Win | 4-6, 6-3, 6-4, 4-6, 6-4 |
| Fourth Round | Dominic Thiem | Loss | 5-7, 2-6, 6-7 (2-7) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jeremy Chardy | Win | 7-6 (8-6), 6-2 |
| Third Round | David Goffin | Loss | 2-6, 4-6 |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Evgeny Donskoy | Win | 4-6, 6-2, 7-6 (7-0) |
| Third Round | Ilya Ivashka | Win | 7-5, 6-3 |
| Quarterfinals | Grigor Dimitrov | Win | 6-2, 6-2 |
| Semifinals | Stefanos Tsitsipas | Loss | 7-6 (7-4), 4-6, 6-7 (7-9) |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Norbert Gombos | Win | 6-3, 6-4, 6-4 |
| Second Round | Andreas Seppi | Win | 6-3, 6-7 (5-7), 6-3, 6-4 |
| Third Round | Philipp Kohlschreiber | Win | 6-3, 7-5, 7-5 |
| Fourth Round | Gael Monfils | Win | 7-6 (7-4), 7-6 (7-2), 5-7, 7-6(7-4) |
| Quarterfinals | Roger Federer | Win | 2-6, 6-7 (5-7), 7-5, 6-4, 13-11 |
| Semifinals | John Isner | Win | 7-6 (8-6), 6-7 (5-7), 6-7 (9-11), 6-4, 26-24 |
| Final | Novak Djokovic | Loss | 2-6, 2-6, 6-7 (3-7) |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Leonardo Mayer | Loss | 6-7 (4-7), 6-4, 6-7 (3-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Paolo Lorenzi | Win | 6-1, 6-2, 6-4 |
| Second Round | Pablo Cuevas | Win | 6-3, 3-6, 7-6 (7-5), 6-4 |
| Third Round | Mischa Zverev | Win | 6-1, 6-7 (3-7), 6-3, 7-6(7-4) |
| Fourth Round | Diego Schwartzman | Loss | 6-1, 6-2, 5-7, 6-7 (0-7), 2-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Aljaz Bedene | Loss | 4-6, 0-0 Retired |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mikhail Kukushkin | Win | 5-7, 7-6 (7-3), 6-2 |
| Third Round | Philipp Kohlschreiber | Win | 6-3, 7-6 (9-7) |
| Quarterfinals | Dusan Lajovic | Win | 7-6 (7-3), 3-6, 6-3 |
| Semifinals | Dominic Thiem | Loss | 4-6, 2-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 30 - May 6 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Stefanos Tsitsipas | Loss | 7-6 (7-3), 3-6, 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Nikoloz Basilashvili | Win | 6-4, 6-3 |
| Third Round | Karen Khachanov | Win | 4-6, 6-2, 6-3 |
| Fourth Round | Frances Tiafoe | Win | 7-6 (7-3), 6-4 |
| Quarterfinals | Pablo Carreno Busta | Loss | 4-6, 7-5, 6-7 (6-8) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Evgeny Donskoy | Win | 7-5, 6-4 |
| Third Round | Nicolas Kicker | Win | 7-6 (7-1), 7-6 (7-3) |
| Fourth Round | Pablo Carreno Busta | Win | 4-6, 6-3, 7-6 (8-6) |
| Quarterfinals | Borna Coric | Loss | 6-2, 4-6, 6-7 (3-7) |
| Abierto Mexicano TELCEL | ||
| Surface: Hard | Date: Feb. 26 - Mar. 3 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Radu Albot | Win | 6-4, 6-3 |
| Second Round | Adrian Mannarino | Win | 6-3, 6-4 |
| Quarterfinals | Hyeon Chung | Win | 7-6 (7-5), 6-4 |
| Semifinals | Jared Donaldson | Win | 6-3, 4-6, 6-3 |
| Final | Juan Martin Del Potro | Loss | 4-6, 4-6 |
| New York Open | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ernesto Escobedo | Win | 3-6, 6-4, 7-6 (7-5) |
| Quarterfinals | Frances Tiafoe | Win | 6-3, 5-7, 6-4 |
| Semifinals | Kei Nishikori | Win | 6-1, 3-6, 7-6 (7-4) |
| Final | Sam Querrey | Win | 4-6, 6-3, 7-6 (7-1) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Kyle Edmund | Loss | 7-6 (7-4), 3-6, 6-3, 3-6, 4-6 |
| Tata Open Maharashtra | ||
| Surface: Hard | Date: Jan. 1 - Jan. 6 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Thiago Monteiro | Win | 7-6 (7-4), 3-2 Retired |
| Quarterfinals | Mikhail Kukushkin | Win | 6-7 (3-7), 6-4, 6-2 |
| Semifinals | Benoit Paire | Win | 6-7 (6-8), 7-6 (7-2), 6-1 |
| Final | Gilles Simon | Loss | 6-7 (4-7), 2-6 |
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