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| Rolex Shanghai Masters | ||
| Surface: Hard | Date: Oct. 6 - Oct. 13 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Cameron Norrie | Win | 6-3, 6-1 |
| Third Round | Vasek Pospisil | Win | 7-6 (9-7), 7-5 |
| Quarterfinals | Fabio Fognini | Win | 6-3, 7-6 (7-4) |
| Semifinals | Stefanos Tsitsipas | Win | 7-6 (7-5), 7-5 |
| Final | Alexander Zverev | Win | 6-4, 6-1 |
| St. Petersburg Open | ||
| Surface: Hard | Date: Sep. 16 - Sep. 22 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Evgeny Donskoy | Win | 7-5, 6-3 |
| Quarterfinals | Andrey Rublev | Win | 6-4, 7-5 |
| Semifinals | Egor Gerasimov | Win | 7-5, 7-5 |
| Final | Borna Coric | Win | 6-3, 6-1 |
| US Open | ||
| Surface: Hard | Date: Aug. 26 - Sep. 8 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Prajnesh Gunneswaran | Win | 6-4, 6-1, 6-2 |
| Second Round | Hugo Dellien | Win | 6-3, 7-5, 5-7, 6-3 |
| Third Round | Feliciano Lopez | Win | 7-6 (7-1), 4-6, 7-6 (9-7), 6-4 |
| Fourth Round | Dominik Koepfer | Win | 3-6, 6-3, 6-2, 7-6(7-2) |
| Quarterfinals | Stan Wawrinka | Win | 7-6 (8-6), 6-3, 3-6, 6-1 |
| Semifinals | Grigor Dimitrov | Win | 7-6 (7-5), 6-4, 6-3 |
| Final | Rafael Nadal | Loss | 5-7, 3-6, 7-5, 6-4, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Kyle Edmund | Win | 6-2, 7-5 |
| Second Round | Benoit Paire | Win | 7-6 (7-2), 6-1 |
| Third Round | Jan-Lennard Struff | Win | 6-2, 6-1 |
| Quarterfinals | Andrey Rublev | Win | 6-2, 6-3 |
| Semifinals | Novak Djokovic | Win | 3-6, 6-3, 6-3 |
| Final | David Goffin | Win | 7-6 (7-3), 6-4 |
| Coupe Rogers presentee par Banque Nationale | ||
| Surface: Hard | Date: Aug. 5 - Aug. 11 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Kyle Edmund | Win | 6-3, 6-0 |
| Third Round | Cristian Garin | Win | 6-3, 6-3 |
| Quarterfinals | Dominic Thiem | Win | 6-3, 6-1 |
| Semifinals | Karen Khachanov | Win | 6-1, 7-6 (8-6) |
| Final | Rafael Nadal | Loss | 3-6, 0-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 29 - Aug. 4 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Bjorn Fratangelo | Win | 6-3, 6-4 |
| Third Round | Frances Tiafoe | Win | 6-2, 7-5 |
| Quarterfinals | Marin Cilic | Win | 6-4, 7-6 (9-7) |
| Semifinals | Peter Gojowczyk | Win | 6-2, 6-2 |
| Final | Nick Kyrgios | Loss | 6-7 (6-8), 6-7 (4-7) |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Paolo Lorenzi | Win | 6-3, 7-6 (7-2), 7-6 (7-2) |
| Second Round | Alexei Popyrin | Win | 6-7 (6-8), 6-1, 6-4, 6-4 |
| Third Round | David Goffin | Loss | 6-4, 2-6, 6-3, 3-6, 5-7 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Fernando Verdasco | Win | 6-2, 6-4 |
| Second Round | Lucas Pouille | Win | 7-6 (11-9), 6-7 (5-7), 6-4 |
| Quarterfinals | Diego Schwartzman | Win | 6-2, 6-2 |
| Semifinals | Gilles Simon | Loss | 7-6 (7-4), 4-6, 3-6 |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 10 - Jun. 16 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Lucas Pouille | Loss | 6-7 (6-8), 6-4, 2-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Loss | 6-4, 6-4, 3-6, 2-6, 5-7 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Nick Kyrgios | Loss | 3-6, 6-3, 3-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Loss | 2-6, 6-1, 3-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 22 - Apr. 28 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Albert Ramos-Vinolas | Win | 6-3, 2-6, 6-1 |
| Third Round | Mackenzie McDonald | Win | 6-3, 6-2 |
| Quarterfinals | Nicolas Jarry | Win | 6-3, 6-4 |
| Semifinals | Kei Nishikori | Win | 6-4, 3-6, 7-5 |
| Final | Dominic Thiem | Loss | 4-6, 0-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Joao Sousa | Win | 6-1, 6-1 |
| Second Round | Radu Albot | Win | 6-1, 6-2 |
| Third Round | Stefanos Tsitsipas | Win | 6-2, 1-6, 6-4 |
| Quarterfinals | Novak Djokovic | Win | 6-3, 4-6, 6-2 |
| Semifinals | Dusan Lajovic | Loss | 5-7, 1-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 13 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Adrian Mannarino | Win | 6-2, 6-1 |
| Third Round | Reilly Opelka | Win | 7-6 (7-5), 6-7 (5-7), 7-6 (7-0) |
| Fourth Round | Roger Federer | Loss | 4-6, 2-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mackenzie McDonald | Win | 7-5, 6-0 |
| Third Round | Filip Krajinovic | Loss | 3-6, 2-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 25 - Mar. 2 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Ricardas Berankis | Loss | 3-6, 3-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 11 - Feb. 17 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Jeremy Chardy | Win | 7-6 (7-2), 6-2 |
| Second Round | Fernando Verdasco | Win | 6-2, 7-5 |
| Quarterfinals | Jo-Wilfried Tsonga | Win | 6-4, 6-2 |
| Semifinals | Gael Monfils | Loss | 6-4, 3-6, 4-6 |
| Garanti Koza Sofia Open | ||
| Surface: Hard | Date: Feb. 4 - Feb. 10 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Robin Haase | Win | 5-7, 6-2, 6-2 |
| Quarterfinals | Martin Klizan | Win | 6-4, 6-1 |
| Semifinals | Gael Monfils | Win | 6-2, 6-4 |
| Final | Marton Fucsovics | Win | 6-4, 6-3 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 14 - Jan. 27 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Lloyd Harris | Win | 6-1, 6-2, 6-1 |
| Second Round | Ryan Harrison | Win | 6-3, 6-3, 6-3 |
| Third Round | David Goffin | Win | 6-2, 7-6 (7-3), 6-3 |
| Fourth Round | Novak Djokovic | Loss | 4-6, 7-6 (7-5), 2-6, 3-6 |
| Sydney International | ||
| Surface: Hard | Date: Jan. 6 - Jan. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Bye |
| Brisbane International presented by Suncorp | ||
| Surface: Hard | Date: Dec. 31 - Jan. 6 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andy Murray | Win | 7-5, 6-2 |
| Quarterfinals | Milos Raonic | Win | 6-7 (2-7), 6-3, 6-4 |
| Semifinals | Jo-Wilfried Tsonga | Win | 7-6 (7-6), 6-2 |
| Final | Kei Nishikori | Loss | 4-6, 6-3, 2-6 |
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