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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Sam Querrey | Loss | 4-6, 7-6 (7-5), 6-7 (5-7) |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pierre-Hugues Herbert | Win | 7-6 (7-3), 6-2 |
| Third Round | Karen Khachanov | Loss | 6-7 (5-7), 6-7 (1-7) |
| Citi Open | ||
| Surface: Hard | Date: Jul. 30 - Aug. 5 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Noah Rubin | Loss | 4-6, 6-7 (6-8) |
| BB&T Atlanta Open | ||
| Surface: Hard | Date: Jul. 23 - Jul. 29 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alex De Minaur | Win | 6-3, 6-2 |
| Quarterfinals | Mischa Zverev | Win | 7-5, 4-6, 6-1 |
| Semifinals | Matthew Ebden | Win | 6-4, 6-7 (6-8), 6-1 |
| Final | Ryan Harrison | Win | 5-7, 6-3, 6-4 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Yannick Maden | Win | 6-2, 7-6 (7-4), 7-5 |
| Second Round | Ruben Bemelmans | Win | 6-1, 6-4, 6-7 (6-8), 6-7(3-7), 7-5 |
| Third Round | Radu Albot | Win | 6-3, 6-3, 6-4 |
| Fourth Round | Stefanos Tsitsipas | Win | 6-4, 7-6 (10-8), 7-6 (7-4) |
| Quarterfinals | Milos Raonic | Win | 6-7 (5-7), 7-6 (9-7), 6-4, 6-3 |
| Semifinals | Kevin Anderson | Loss | 6-7 (6-8), 7-6 (7-5), 7-6 (11-9), 4-6, 24-26 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Noah Rubin | Win | 6-3, 7-6 (9-7), 7-6 (9-7) |
| Second Round | Horacio Zeballos | Win | 6-7 (8-10), 7-6 (7-4), 7-6 (7-2), 6-2 |
| Third Round | Pierre-Hugues Herbert | Win | 7-6 (7-1), 6-4, 7-6 (7-4) |
| Fourth Round | Juan Martin Del Potro | Loss | 4-6, 4-6, 4-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 20 - May 26 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Radu Albot | Win | 7-6 (7-3), 6-3 |
| Quarterfinals | Cameron Norrie | Loss | 6-7 (1-7), 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Albert Ramos-Vinolas | Loss | 7-6 (7-5), 6-7 (2-7), 6-7 (5-7) |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ryan Harrison | Win | 7-6 (7-1), 7-6 (9-7) |
| Third Round | Pablo Cuevas | Win | 6-7 (9-11), 7-6 (7-3), 7-6 (7-4) |
| Quarterfinals | Alexander Zverev | Loss | 4-6, 5-7 |
| Fayez Sarofim & Co. US Men's Clay Court Championship | ||
| Surface: Clay | Date: Apr. 9 - Apr. 15 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Henri Laaksonen | Win | 6-4, 6-2 |
| Quarterfinals | Steve Johnson | Loss | 6-7 (4-7), 6-4, 6-7 (5-7) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jiri Vesely | Win | 7-6 (7-3), 1-6, 6-3 |
| Third Round | Mikhail Youzhny | Win | 6-4, 6-3 |
| Fourth Round | Marin Cilic | Win | 7-6 (7-0), 6-3 |
| Quarterfinals | Hyeon Chung | Win | 6-1, 6-4 |
| Semifinals | Juan Martin Del Potro | Win | 6-1, 7-6 (7-2) |
| Final | Alexander Zverev | Win | 6-7 (4-7), 6-4, 6-4 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Gael Monfils | Loss | 7-6 (7-5), 6-7 (3-7), 5-7 |
| Abierto Mexicano TELCEL | ||
| Surface: Hard | Date: Feb. 26 - Mar. 3 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Ryan Harrison | Loss | 3-6, 6-7 (5-7) |
| Delray Beach Open | ||
| Surface: Hard | Date: Feb. 19 - Feb. 25 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Radu Albot | Win | 5-7, 6-3, 6-4 |
| Second Round | Peter Gojowczyk | Loss | 6-7 (3-7), 7-6 (7-4), 6-7 (5-7) |
| New York Open | ||
| Surface: Hard | Date: Feb. 12 - Feb. 18 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Radu Albot | Loss | 6-7 (5-7), 6-3, 3-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Matthew Ebden | Loss | 4-6, 6-3, 3-6, 3-6 |
| ASB Classic | ||
| Surface: Hard | Date: Jan. 1 - Jan. 13 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Hyeon Chung | Loss | 6-7 (3-7), 7-5, 2-6 |
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