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| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 14 - Aug. 21 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Holger Rune | Win | 7-6 (7-5), 4-6, 6-4 |
| Second Round | Andy Murray | Win | 3-6, 6-3, 6-4 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 8 - Aug. 14 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Brandon Nakashima | Win | 6-4, 6-4 |
| Second Round | Botic van de Zandschulp | Win | 6-1, 6-2 |
| Third Round | Felix Auger-Aliassime | Loss | 3-6, 4-6 |
| Abierto de Tenis Mifel | ||
| Surface: Hard | Date: Aug. 1 - Aug. 6 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Chun-hsin Tseng | Win | 6-3, 6-0 |
| Quarterfinals | Radu Albot | Win | 6-3, 7-6 (7-4) |
| Semifinals | Felix Auger-Aliassime | Win | 6-4, 3-6, 6-3 |
| Final | Daniil Medvedev | Loss | 5-7, 0-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 27 - Jul. 10 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Pablo Andujar | Win | 6-0, 7-6 (7-3), 6-3 |
| Second Round | Jaume Munar | Win | 6-4, 3-6, 5-7, 6-0, 6-2 |
| Third Round | Steve Johnson | Win | 6-4, 6-1, 6-0 |
| Fourth Round | Tommy Paul | Win | 6-4, 7-5, 6-4 |
| Quarterfinals | David Goffin | Win | 3-6, 7-5, 2-6, 6-3, 7-5 |
| Semifinals | Novak Djokovic | Loss | 6-2, 3-6, 2-6, 4-6 |
| Rothesay International Eastbourne | ||
| Surface: Grass | Date: Jun. 19 - Jun. 25 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Brandon Nakashima | Win | 6-4, 6-2 |
| Quarterfinals | Maxime Cressy | Loss | 5-7, 5-7 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 7-6 (7-2), 1-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Manuel Guinard | Win | 7-5, 6-2, 6-0 |
| Second Round | Jason Kubler | Win | 6-3, 6-4, 6-3 |
| Third Round | Karen Khachanov | Loss | 2-6, 5-7, 7-5, 4-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 15 - May 21 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Francisco Cerundolo | Win | 6-4, 6-4 |
| Quarterfinals | Sebastian Baez | Win | 6-4, 4-6, 7-5 |
| Semifinals | Holger Rune | Win | 6-2, 5-7, 6-4 |
| Final | Alex Molcan | Win | 6-3, 6-7 (3-7), 6-1 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Luca Nardi | Win | 6-4, 6-4 |
| Second Round | Marin Cilic | Loss | 7-5, 2-6, 1-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Soon Woo Kwon | Win | 7-5, 7-5 |
| Second Round | John Isner | Win | 6-4, 6-7 (5-7), 6-4 |
| Third Round | Carlos Alcaraz | Loss | 4-6, 7-6 (7-4), 3-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Egor Gerasimov | Win | 5-7, 6-4, 6-4 |
| Third Round | Marton Fucsovics | Win | 7-5, 6-7 (9-11), 6-4 |
| Quarterfinals | Alex De Minaur | Loss | 3-6, 7-5, 1-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Albert Ramos-Vinolas | Loss | 4-6, 6-2, 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 10 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jack Draper | Win | 7-6 (7-5), 6-4 |
| Third Round | Hugo Gaston | Win | 6-3, 7-5 |
| Fourth Round | Casper Ruud | Loss | 3-6, 4-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pedro Martinez | Win | 6-3, 6-3 |
| Third Round | Nikoloz Basilashvili | Win | 3-6, 6-3, 6-1 |
| Fourth Round | Jenson Brooksby | Win | 6-2, 6-4 |
| Quarterfinals | Carlos Alcaraz | Loss | 4-6, 3-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Daniel Altmaier | Win | 7-6 (7-5), 6-2 |
| Second Round | John Isner | Win | 6-7 (2-7), 6-3, 6-4 |
| Quarterfinals | Peter Gojowczyk | Win | 6-1, 6-0 |
| Semifinals | Stefanos Tsitsipas | Win | 6-4, 6-4 |
| Final | Rafael Nadal | Loss | 4-6, 4-6 |
| Delray Beach Open by VITACOST.com | ||
| Surface: Hard | Date: Feb. 14 - Feb. 20 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Oscar Otte | Win | 6-3, 7-5 |
| Quarterfinals | Sebastian Korda | Win | 6-2, 1-6, 7-6 (7-4) |
| Semifinals | Tommy Paul | Win | 6-3, 6-3 |
| Final | Reilly Opelka | Win | 7-6 (7-1), 7-6 (7-4) |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Win | 6-2, 6-4 |
| Second Round | Karen Khachanov | Win | 6-4, 7-6 (7-5) |
| Quarterfinals | Felix Auger-Aliassime | Loss | 5-7, 6-7 (4-7) |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Sebastian Korda | Loss | 3-6, 0-6, 4-6 |
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