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| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Roberto Carballes Baena | Win | 6-1, 6-2 |
| Third Round | Lloyd Harris | Win | 6-7 (4-7), 6-4, 6-4 |
| Fourth Round | Diego Schwartzman | Loss | 3-6, 3-6 |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andy Murray | Win | 7-5, 6-4 |
| Quarterfinals | Lorenzo Sonego | Win | 6-1, 6-4 |
| Semifinals | Grigor Dimitrov | Win | 6-4, 4-6, 6-4 |
| Final | Cameron Norrie | Win | 6-0, 6-2 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Yuichi Sugita | Win | 6-3, 6-2, 6-2 |
| Second Round | Botic van de Zandschulp | Loss | 6-3, 4-6, 3-6, 4-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Reilly Opelka | Win | 6-7 (5-7), 6-0, 7-6 (7-4) |
| Third Round | Diego Schwartzman | Win | 6-4, 6-3 |
| Quarterfinals | Alexander Zverev | Loss | 1-6, 3-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marin Cilic | Win | 6-3, 3-6, 6-3 |
| Third Round | Dusan Lajovic | Win | 6-4, 6-3 |
| Quarterfinals | Stefanos Tsitsipas | Loss | 1-6, 4-6 |
| Generali Open | ||
| Surface: Clay | Date: Jul. 26 - Jul. 31 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Mario Vilella Martinez | Win | 7-5, 5-7, 6-4 |
| Quarterfinals | Mikael Ymer | Win | 3-6, 7-6 (7-5), 6-1 |
| Semifinals | Arthur Rinderknech | Win | 6-3, 7-6 (9-7) |
| Final | Pedro Martinez | Win | 6-1, 4-6, 6-3 |
| J. Safra Sarasin Suisse Open Gstaad | ||
| Surface: Clay | Date: Jul. 19 - Jul. 25 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Dennis Novak | Win | 6-4, 7-6 (7-5) |
| Quarterfinals | Benoit Paire | Win | 6-2, 5-7, 6-3 |
| Semifinals | Vit Kopriva | Win | 6-3, 6-0 |
| Final | Hugo Gaston | Win | 6-3, 6-2 |
| Nordea Open | ||
| Surface: Clay | Date: Jul. 12 - Jul. 18 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Holger Vitus Nodskov Rune | Win | 6-0, 6-2 |
| Quarterfinals | Henri Laaksonen | Win | Retired |
| Semifinals | Roberto Carballes Baena | Win | 6-1, 6-4 |
| Final | Federico Coria | Win | 6-3, 6-3 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Jordan Thompson | Loss | 6-7 (6-8), 6-7 (3-7), 6-2, 6-2, 2-6 |
| Mallorca Championships | ||
| Surface: Grass | Date: Jun. 20 - Jun. 26 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Gilles Simon | Win | 6-4, 7-6 (7-4) |
| Second Round | Tennys Sandgren | Win | 6-3, 6-4 |
| Quarterfinals | Daniil Medvedev | Loss | 5-7, 1-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Benoit Paire | Win | 5-7, 6-2, 6-1, 7-6(7-4) |
| Second Round | Kamil Majchrzak | Win | 6-3, 6-2, 6-4 |
| Third Round | Alejandro Davidovich Fokina | Loss | 6-7 (3-7), 6-2, 6-7 (6-8), 6-0, 5-7 |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 16 - May 22 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Tennys Sandgren | Win | 7-5, 6-2 |
| Quarterfinals | Dominik Koepfer | Win | 2-6, 6-1, 6-4 |
| Semifinals | Pablo Andujar | Win | 6-3, 6-2 |
| Final | Denis Shapovalov | Win | 7-6 (8-6), 6-4 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Felix Auger-Aliassime | Win | 6-1, 6-4 |
| Second Round | Yoshihito Nishioka | Win | 6-1, 6-2 |
| Third Round | Stefanos Tsitsipas | Win | 7-6 (7-4), 6-4 |
| Quarterfinals | Alexander Bublik | Win | 7-5, 6-1 |
| Semifinals | Matteo Berrettini | Loss | 4-6, 4-6 |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pablo Cuevas | Win | 6-3, 6-2 |
| Quarterfinals | John Millman | Win | 6-3, 6-4 |
| Semifinals | Nikoloz Basilashvili | Loss | 1-6, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Holger Vitus Nodskov Rune | Win | 6-2, 6-1 |
| Second Round | Diego Schwartzman | Win | 6-3, 6-3 |
| Third Round | Pablo Carreno Busta | Win | 7-6 (7-4), 5-7, 7-5 |
| Quarterfinals | Fabio Fognini | Win | 6-4, 6-3 |
| Semifinals | Andrey Rublev | Loss | 3-6, 5-7 |
| AnyTech365 Andalucia Open | ||
| Surface: Red Clay | Date: Apr. 5 - Apr. 11 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Gianluca Mager | Win | 6-3, 6-2 |
| Quarterfinals | Carlos Alcaraz | Loss | 2-6, 4-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Daniel Elahi Galan | Win | 6-4, 6-1 |
| Second Round | Tallon Griekspoor | Win | 4-6, 6-3, 7-6 (7-3) |
| Quarterfinals | Alexander Zverev | Loss | Retired |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: 24 |
| Round | Opponent | W / L | Result |
| First Round | Jordan Thompson | Win | 6-3, 6-3, 2-1 Retired |
| Second Round | Tommy Paul | Win | 3-6, 6-2, 6-4, 7-5 |
| Third Round | Radu Albot | Win | 6-1, 5-7, 6-4, 6-4 |
| Fourth Round | Andrey Rublev | Loss | 2-6, 6-7 (3-7), 0-0 Retired |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jiri Vesely | Loss | 7-5, 6-7 (4-7), 3-6 |
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