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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Win | 7-5, 6-3 |
| Second Round | Benoit Paire | Win | 5-7, 6-4, 6-2 |
| Third Round | Kevin Anderson | Win | 6-2, 6-4 |
| Quarterfinals | Juan Martin Del Potro | Win | 7-6 (7-5), 7-6 (7-4) |
| Semifinals | Roger Federer | Loss | 6-7 (3-7), 1-1 Retired |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Milos Raonic | Loss | 3-6, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 30 - Aug. 5 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pierre-Hugues Herbert | Win | 6-2, 1-6, 7-6 (7-5) |
| Third Round | Frances Tiafoe | Win | 6-0, 6-3 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 3-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Matthew Ebden | Loss | 4-6, 3-6, 4-6 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Feliciano Lopez | Loss | 3-6, 7-6 (9-7), 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Robin Haase | Win | 4-6, 4-6, 6-4, 6-1, 6-0 |
| Second Round | Corentin Moutet | Win | 7-5, 6-0, 6-1 |
| Third Round | Gael Monfils | Win | 6-7 (6-8), 6-3, 4-6, 7-5, 6-3 |
| Fourth Round | Marco Cecchinato | Loss | 5-7, 6-4, 0-6, 3-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Leonardo Mayer | Win | 6-1, 6-2 |
| Second Round | Marco Cecchinato | Win | 5-7, 6-2, 6-2 |
| Third Round | Juan Martin Del Potro | Win | 6-2, 4-5 Retired |
| Quarterfinals | Alexander Zverev | Loss | 4-6, 6-3, 3-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Robin Haase | Win | 7-5, 6-3 |
| Third Round | Kyle Edmund | Loss | 3-6, 3-6 |
| Barcelona Open Banco Sabadell | ||
| Surface: Clay | Date: Apr. 23 - Apr. 29 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marcel Granollers | Win | 4-6, 7-6 (7-2), 6-2 |
| Third Round | Karen Khachanov | Win | 2-6, 7-6 (7-2), 6-0 |
| Quarterfinals | Roberto Bautista Agut | Win | 6-7 (3-7), 6-2, 6-2 |
| Semifinals | Rafael Nadal | Loss | 4-6, 0-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Stefanos Tsitsipas | Win | 7-6 (7-4), 7-5 |
| Third Round | Roberto Bautista Agut | Win | 6-4, 7-5 |
| Quarterfinals | Grigor Dimitrov | Loss | 4-6, 6-7 (5-7) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Joao Sousa | Loss | 0-6, 1-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Nicolas Mahut | Win | 6-1, 6-3 |
| Second Round | Feliciano Lopez | Win | 6-1, 6-3 |
| Quarterfinals | Tomas Berdych | Win | Retired |
| Semifinals | Grigor Dimitrov | Loss | 3-6, 1-0 Retired |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 5 - Feb. 11 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Gilles Simon | Win | 6-4, 6-2 |
| Quarterfinals | Karen Khachanov | Win | 6-4, 6-4 |
| Semifinals | Richard Gasquet | Loss | 4-6, 6-0, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Matthias Bachinger | Win | 6-7 (3-7), 6-3, 6-2, 6-4 |
| Second Round | Julien Benneteau | Loss | 6-1, 6-7 (5-7), 1-6, 6-7 (4-7) |
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