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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andrey Rublev | Win | 7-5, 6-3 |
| Second Round | Stan Wawrinka | Loss | 4-6, 4-6 |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Robin Haase | Loss | 5-7, 1-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 30 - Aug. 5 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Donald Young | Win | 6-3, 6-4 |
| Third Round | Denis Shapovalov | Win | 7-6 (7-1), 6-3 |
| Quarterfinals | Alexander Zverev | Loss | 6-3, 1-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: 24 |
| Round | Opponent | W / L | Result |
| First Round | Christian Harrison | Win | 6-2, 4-6, 7-6 (7-3), 6-2 |
| Second Round | Bernard Tomic | Win | 2-6, 6-3, 7-6 (9-7), 7-5 |
| Third Round | Nick Kyrgios | Win | 6-1, 7-6 (7-3), 6-4 |
| Fourth Round | Ernests Gulbis | Win | 4-6, 7-6 (7-5), 7-6 (12-10), 6-1 |
| Quarterfinals | Novak Djokovic | Loss | 3-6, 6-3, 2-6, 2-6 |
| Gerry Weber Open | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Matthias Bachinger | Win | 6-3, 7-6 (7-3) |
| Second Round | Karen Khachanov | Loss | 2-6, 2-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 19 |
| Round | Opponent | W / L | Result |
| First Round | Maxime Janvier | Win | 7-6 (7-0), 6-4, 6-3 |
| Second Round | Benoit Paire | Win | 6-3, 2-6, 4-6, 6-2, 6-3 |
| Third Round | Gilles Simon | Win | 6-3, 6-1, 6-3 |
| Fourth Round | Dominic Thiem | Loss | 2-6, 0-6, 7-5, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Feliciano Lopez | Win | 7-6 (7-5), 6-4 |
| Second Round | Grigor Dimitrov | Win | 6-7 (4-7), 7-5, 6-4 |
| Third Round | Philipp Kohlschreiber | Win | 6-1, 6-2 |
| Quarterfinals | Novak Djokovic | Loss | 6-2, 1-6, 3-6 |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Novak Djokovic | Loss | 5-7, 4-6 |
| Barcelona Open Banco Sabadell | ||
| Surface: Clay | Date: Apr. 23 - Apr. 29 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Guillermo Garcia-Lopez | Loss | 3-6, 0-0 Retired |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tomas Berdych | Win | 4-6, 6-2, 6-1 |
| Second Round | Daniil Medvedev | Win | 7-5, 6-2 |
| Third Round | Andreas Seppi | Win | 6-0, 2-6, 6-3 |
| Quarterfinals | Marin Cilic | Win | 6-4, 6-7 (1-7), 6-3 |
| Semifinals | Alexander Zverev | Win | 3-6, 6-3, 6-4 |
| Final | Rafael Nadal | Loss | 3-6, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | John Millman | Win | 7-6 (7-4), 4-6, 6-3 |
| Third Round | Juan Martin Del Potro | Loss | 2-6, 2-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Bye |
| Abierto Mexicano TELCEL | ||
| Surface: Hard | Date: Feb. 26 - Mar. 3 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Loss | 7-6 (7-3), 3-6, 1-6 |
| New York Open | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Noah Rubin | Win | 7-5, 6-3 |
| Second Round | Evgeny Donskoy | Win | 6-2, 6-4 |
| Quarterfinals | Radu Albot | Win | 4-6, 6-3, 6-1 |
| Semifinals | Kevin Anderson | Loss | 1-6, 6-3, 6-7 (4-7) |
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