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| US Open | ||
| Surface: Hard | Date: Aug. 27 - Sep. 9 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Paolo Lorenzi | Loss | 6-4, 4-6, 5-7, 1-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 19 - Aug. 25 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Leonardo Mayer | Win | 6-3, 6-3 |
| Third Round | Roberto Carballes Baena | Win | 7-5, 7-5 |
| Quarterfinals | Steve Johnson | Loss | 1-6, 2-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 12 - Aug. 19 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Mackenzie McDonald | Win | 6-3, 6-2 |
| Second Round | Denis Shapovalov | Loss | 4-6, 5-7 |
| Rogers Cup presented by National Bank | ||
| Surface: Hard | Date: Aug. 6 - Aug. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Diego Schwartzman | Loss | 1-6, 2-6 |
| Citi Open | ||
| Surface: Hard | Date: Jul. 30 - Aug. 5 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andy Murray | Loss | 6-7 (4-7), 6-1, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jul. 2 - Jul. 15 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Alex Bolt | Win | 6-2, 6-3, 7-5 |
| Second Round | Bradley Klahn | Win | 6-4, 7-6 (7-0), 6-2 |
| Third Round | Novak Djokovic | Loss | 6-4, 3-6, 2-6, 4-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 24 - Jun. 30 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andy Murray | Win | 6-4, 6-4 |
| Quarterfinals | Mikhail Kukushkin | Loss | 7-5, 3-6, 1-6 |
| Fever-Tree Championships | ||
| Surface: Grass | Date: Jun. 18 - Jun. 24 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Ryan Harrison | Win | 7-6 (7-4), 6-4 |
| Second Round | Nick Kyrgios | Loss | 6-7 (3-7), 7-6 (7-5), 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 27 - Jun. 10 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Alex De Minaur | Win | 6-2, 6-4, 6-3 |
| Second Round | Marton Fucsovics | Win | 6-0, 1-6, 6-2, 6-3 |
| Third Round | Fabio Fognini | Loss | 3-6, 6-4, 6-3, 4-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 13 - May 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Malek Jaziri | Win | 6-3, 3-6, 6-3 |
| Second Round | Lucas Pouille | Win | 6-2, 7-6 (7-3) |
| Third Round | Alexander Zverev | Loss | 5-7, 6-7 (11-13) |
| Mutua Madrid Open | ||
| Surface: Red Clay | Date: May 5 - May 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniil Medvedev | Win | 6-4, 6-0 |
| Second Round | Novak Djokovic | Win | 6-3, 2-6, 6-3 |
| Third Round | David Goffin | Win | 6-3, 6-3 |
| Quarterfinals | Denis Shapovalov | Loss | 5-7, 7-6 (8-6), 4-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 30 - May 6 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alex De Minaur | Win | 6-2, 7-5 |
| Quarterfinals | Joao Sousa | Loss | 3-6, 6-1, 0-6 |
| Monte-Carlo Rolex Masters | ||
| Surface: Clay | Date: Apr. 15 - Apr. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andreas Seppi | Loss | 3-6, 7-5, 2-6 |
| Grand Prix Hassan II | ||
| Surface: Red Clay | Date: Apr. 9 - Apr. 15 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Jiri Vesely | Win | 5-0 Retired |
| Second Round | Radu Albot | Win | 6-2, 6-4 |
| Quarterfinals | Malek Jaziri | Win | 6-2, 6-1 |
| Semifinals | Richard Gasquet | Win | 6-3, 6-4 |
| Final | Pablo Andujar | Loss | 2-6, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 20 - Apr. 1 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Frances Tiafoe | Loss | 6-7 (4-7), 6-4, 6-7 (5-7) |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 7 - Mar. 18 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Dudi Sela | Loss | 4-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 15 - Jan. 28 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Kevin Anderson | Win | 6-7 (4-7), 6-3, 3-6, 6-3, 6-4 |
| Second Round | Denis Istomin | Win | 6-2, 6-2, 6-4 |
| Third Round | Nikoloz Basilashvili | Win | 7-6 (7-0), 3-6, 4-6, 6-0, 7-5 |
| Fourth Round | Andreas Seppi | Win | 6-7 (4-7), 7-5, 6-2, 6-3 |
| Quarterfinals | Grigor Dimitrov | Win | 6-4, 3-6, 6-3, 6-4 |
| Semifinals | Marin Cilic | Loss | 2-6, 6-7 (4-7), 2-6 |
| Brisbane International presented by Suncorp | ||
| Surface: Hard | Date: Dec. 31 - Jan. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Win | 6-7 (5-7), 7-6 (7-4), 6-4 |
| Second Round | Hyeon Chung | Win | 7-6 (7-3), 5-7, 6-4 |
| Quarterfinals | Grigor Dimitrov | Loss | 3-6, 7-6 (7-3), 4-6 |
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