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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 11 - Aug. 18 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Hubert Hurkacz | Win | 7-6 (8-6), 6-3 |
| Second Round | Frances Tiafoe | Win | 6-3, 3-6, 6-1 |
| Third Round | Miomir Kecmanovic | Win | 6-1, 6-2 |
| Quarterfinals | Richard Gasquet | Loss | 6-7 (2-7), 6-3, 2-6 |
| Coupe Rogers presentee par Banque Nationale | ||
| Surface: Hard | Date: Aug. 5 - Aug. 11 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Bernard Tomic | Win | 6-3, 6-2 |
| Second Round | Diego Schwartzman | Win | 6-2, 7-5 |
| Third Round | Richard Gasquet | Win | 7-5, 7-5 |
| Quarterfinals | Gael Monfils | Loss | 4-6, 6-3, 6-7 (2-7) |
| J. Safra Sarasin Suisse Open Gstaad | ||
| Surface: Clay | Date: Jul. 22 - Jul. 28 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jaume Munar | Win | 7-6 (9-7), 6-4 |
| Quarterfinals | Joao Sousa | Loss | 6-4, 3-6, 5-7 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 1 - Jul. 14 | Seed: 23 |
| Round | Opponent | W / L | Result |
| First Round | Peter Gojowczyk | Win | 6-3, 6-2, 6-3 |
| Second Round | Steve Darcis | Win | 6-3, 6-2, 4-2 Retired |
| Third Round | Karen Khachanov | Win | 6-3, 7-6 (7-3), 6-1 |
| Fourth Round | Benoit Paire | Win | 6-3, 7-5, 6-2 |
| Quarterfinals | Guido Pella | Win | 7-5, 6-4, 3-6, 6-3 |
| Semifinals | Novak Djokovic | Loss | 2-6, 6-4, 3-6, 2-6 |
| Noventi Open | ||
| Surface: Grass | Date: Jun. 17 - Jun. 23 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Taylor Fritz | Win | 7-6 (12-10), 6-0 |
| Second Round | Richard Gasquet | Win | 6-1, 6-4 |
| Quarterfinals | Roger Federer | Loss | 3-6, 6-4, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 26 - Jun. 9 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Steve Johnson | Win | 6-3, 6-4, 6-2 |
| Second Round | Taylor Fritz | Win | 6-2, 6-3, 6-2 |
| Third Round | Fabio Fognini | Loss | 6-7 (5-7), 4-6, 6-4, 1-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 19 - May 25 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Corentin Moutet | Win | 4-6, 6-4, 6-3 |
| Quarterfinals | Taylor Fritz | Loss | 7-6 (8-6), 3-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 12 - May 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Win | 6-1, 3-6, 6-1 |
| Second Round | Karen Khachanov | Loss | 7-5, 4-6, 2-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 4 - May 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Ferrer | Loss | 4-6, 6-4, 4-6 |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 29 - May 5 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Rudolf Molleker | Win | 6-4, 6-2 |
| Quarterfinals | Guido Pella | Win | 4-6, 6-4, 6-0 |
| Semifinals | Matteo Berrettini | Loss | 4-6, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 14 - Apr. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | John Millman | Win | 3-6, 6-1, 6-1 |
| Second Round | Rafael Nadal | Loss | 1-6, 1-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 19 - Mar. 31 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Janko Tipsarevic | Win | 7-6 (7-3), 6-4 |
| Third Round | Fabio Fognini | Win | 6-4, 6-4 |
| Fourth Round | Novak Djokovic | Win | 1-6, 7-5, 6-3 |
| Quarterfinals | John Isner | Loss | 6-7 (1-7), 6-7 (5-7) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 6 - Mar. 17 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Yoshihito Nishioka | Loss | 6-7 (3-7), 4-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 25 - Mar. 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ramkumar Ramanathan | Win | 6-4, 6-3 |
| Second Round | Nikoloz Basilashvili | Loss | 7-6 (7-2), 4-6, 3-6 |
| 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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