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| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 13 |
| Round | Opponent | W / L | Result |
| First Round | Max Purcell | Win | 6-4, 6-2, 4-6, 6-2 |
| Second Round | Zachary Svajda | Win | 6-3, 7-6 (7-2), 6-7 (6-8), 6-4 |
| Third Round | Gael Monfils | Win | 7-6 (7-1), 6-2, 4-6, 4-6, 6-4 |
| Fourth Round | Alexander Zverev | Loss | 4-6, 4-6, 6-7 (7-9) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Federico Delbonis | Win | 6-2, 7-5 |
| Second Round | John Isner | Loss | 7-5, 6-7 (4-7), 4-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | James Duckworth | Loss | 3-6, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Aug. 2 - Aug. 8 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Emil Ruusuvuori | Win | 6-2, 6-4 |
| Third Round | Sebastian Korda | Win | 7-6 (7-3), 7-6 (7-3) |
| Quarterfinals | Steve Johnson | Win | 6-4, 6-2 |
| Semifinals | Jenson Brooksby | Win | 7-6 (7-2), 6-1 |
| Final | Mackenzie McDonald | Win | 7-5, 4-6, 7-5 |
| Truist Atlanta Open | ||
| Surface: Hard | Date: Jul. 26 - Aug. 1 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Christopher O'Connell | Loss | 6-7 (7-9), 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 19 |
| Round | Opponent | W / L | Result |
| First Round | Marton Fucsovics | Loss | 7-5, 3-6, 5-7, 3-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Jack Draper | Loss | 6-7 (6-8), 6-7 (2-7) |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Pierre-Hugues Herbert | Win | 6-1, 4-6, 6-7 (4-7), 7-5, 6-4 |
| Second Round | Gianluca Mager | Win | 6-1, 7-5, 3-6, 6-3 |
| Third Round | Mikael Ymer | Win | 6-1, 7-5, 6-3 |
| Fourth Round | Rafael Nadal | Loss | 5-7, 3-6, 0-6 |
| Open Parc Auvergne-Rhone-Alpes Lyon | ||
| Surface: Clay | Date: May 17 - May 23 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Win | 0-6, 6-3, 6-4 |
| Second Round | Arthur Rinderknech | Loss | 7-6 (9-7), 2-6, 5-7 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Win | 6-2, 6-4 |
| Second Round | Rafael Nadal | Loss | 5-7, 4-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: 14 |
| Round | Opponent | W / L | Result |
| First Round | Guido Pella | Win | 6-2, 4-4 Retired |
| Second Round | Alexei Popyrin | Loss | 6-7 (5-7), 2-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: 11 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Egor Gerasimov | Win | 6-3, 6-2 |
| Third Round | Roberto Bautista Agut | Win | 7-6 (11-9), 6-2 |
| Quarterfinals | Andrey Rublev | Win | 6-2, 7-6 (8-6) |
| Semifinals | Stefanos Tsitsipas | Loss | 3-6, 3-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | 6-3, 6-4 |
| Second Round | Novak Djokovic | Loss | 4-6, 2-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Hugo Gaston | Win | 6-2, 6-2 |
| Third Round | Karen Khachanov | Win | 4-6, 7-6 (7-2), 6-4 |
| Fourth Round | Emil Ruusuvuori | Win | 6-3, 6-2 |
| Quarterfinals | Alexander Bublik | Win | 7-6 (7-5), 6-4 |
| Semifinals | Roberto Bautista Agut | Win | 5-7, 6-4, 6-4 |
| Final | Hubert Hurkacz | Loss | 6-7 (4-7), 4-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Mar. 14 - Mar. 20 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Alexander Bublik | Win | 2-6, 7-6 (7-2), 6-4 |
| Third Round | Roberto Bautista Agut | Win | 6-4, 3-6, 7-5 |
| Quarterfinals | Aslan Karatsev | Loss | 7-6 (7-5), 3-6, 2-6 |
| Open 13 Provence | ||
| Surface: Hard | Date: Mar. 8 - Mar. 14 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Gregoire Barrere | Win | 7-6 (7-3), 6-7 (5-7), 7-5 |
| Second Round | Hugo Gaston | Win | 6-4, 6-1 |
| Quarterfinals | Daniil Medvedev | Loss | 2-6, 4-6 |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 22 - Feb. 28 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Aljaz Bedene | Loss | 6-3, 2-6, 6-7 (3-7) |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Loss | 6-3, 3-6, 2-6, 6-4, 4-6 |
| Great Ocean Road Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Aleksandar Vukic | Win | 6-2, 6-4 |
| Third Round | Aljaz Bedene | Win | 7-6 (8-6), 6-2 |
| Quarterfinals | Miomir Kecmanovic | Win | 7-6 (12-10), 6-4 |
| Semifinals | Karen Khachanov | Win | 7-6 (7-4), 4-6, 7-6 (7-4) |
| Final | Stefano Travaglia | Win | 7-6 (7-4), 6-4 |
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