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| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 17 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Kevin Anderson | Loss | 6-7 (7-9), 6-7 (3-7) |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 6-3, 6-4 |
| Second Round | Sebastian Korda | Win | 6-4, 6-3 |
| Quarterfinals | Casper Ruud | Loss | 1-6, 4-6 |
| Moselle Open | ||
| Surface: Hard | Date: Sep. 20 - Sep. 26 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Marton Fucsovics | Win | 6-3, 6-2 |
| Second Round | Holger Vitus Nodskov Rune | Loss | 7-6 (8-6), 4-6, 4-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 20 |
| Round | Opponent | W / L | Result |
| First Round | Oscar Otte | Loss | 7-6 (10-8), 5-7, 6-7 (4-7), 6-7 (1-7) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Carlos Alcaraz | Win | 6-3, 7-6 (8-6) |
| Second Round | Tommy Paul | Win | 7-6 (11-9), 6-2 |
| Third Round | Stefanos Tsitsipas | Loss | 7-5, 3-6, 4-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Loss | 3-6, 4-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 23 |
| Round | Opponent | W / L | Result |
| First Round | Pedro Sousa | Win | 6-2, 7-5, 6-0 |
| Second Round | Daniel Elahi Galan | Win | 4-6, 6-3, 7-6 (7-3), 6-1 |
| Third Round | James Duckworth | Win | 6-3, 6-4, 6-4 |
| Fourth Round | Roger Federer | Loss | 5-7, 4-6, 2-6 |
| Nature Valley International | ||
| Surface: Grass | Date: Jun. 21 - Jun. 26 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | John Millman | Win | 6-4, 6-2 |
| Quarterfinals | Alexander Bublik | Win | 6-1, 7-5 |
| Semifinals | Max Purcell | Win | 6-1, 3-6, 6-1 |
| Final | Alex De Minaur | Loss | 6-4, 4-6, 6-7 (5-7) |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Viktor Troicki | Loss | 4-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: 26 |
| Round | Opponent | W / L | Result |
| First Round | Lloyd Harris | Loss | 5-7, 4-6, 4-6 |
| Emilia-Romagna Open | ||
| Surface: Clay | Date: May 17 - May 29 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Sebastian Korda | Loss | 1-6, 5-7 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gael Monfils | Win | 6-4, 5-7, 6-4 |
| Second Round | Gianluca Mager | Win | 6-4, 6-4 |
| Third Round | Dominic Thiem | Win | 6-4, 6-7 (5-7), 7-6 (7-5) |
| Quarterfinals | Andrey Rublev | Win | 3-6, 6-4, 6-3 |
| Semifinals | Novak Djokovic | Loss | 3-6, 7-6 (7-5), 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marton Fucsovics | Win | 6-3, 6-4 |
| Second Round | Alexander Zverev | Loss | 3-6, 3-6 |
| Sardegna Open | ||
| Surface: Red Clay | Date: Apr. 5 - Apr. 11 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Gilles Simon | Win | 6-4, 6-1 |
| Quarterfinals | Yannick Hanfmann | Win | 3-6, 7-6 (8-6), 6-3 |
| Semifinals | Taylor Fritz | Win | 6-4, 5-7, 6-1 |
| Final | Laslo Djere | Win | 2-6, 7-6 (7-5), 6-4 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 24 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Bjorn Fratangelo | Win | 6-4, 7-6 (7-5) |
| Third Round | Daniel Elahi Galan | Win | 7-6 (8-6), 6-3 |
| Fourth Round | Stefanos Tsitsipas | Loss | 2-6, 6-7 (2-7) |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Mar. 14 - Mar. 20 | Seed: 17 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Bernabe Zapata Miralles | Win | 6-2, 6-2 |
| Third Round | Aslan Karatsev | Loss | 6-3, 3-6, 4-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taylor Fritz | Loss | 6-7 (5-7), 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Mar. 1 - Mar. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tommy Paul | Loss | 4-6, 6-7 (7-9) |
| Open Sud de France | ||
| Surface: Hard | Date: Feb. 22 - Feb. 28 | Seed: 7 |
| Round | Opponent | W / L | Result |
| First Round | Hugo Gaston | Win | 6-3, 6-7 (7-9), 6-1 |
| Second Round | Sebastian Korda | Win | 6-3, 6-2 |
| Quarterfinals | David Goffin | Loss | 4-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: 31 |
| Round | Opponent | W / L | Result |
| First Round | Sam Querrey | Win | 7-5, 6-4, 6-4 |
| Second Round | Feliciano Lopez | Loss | 7-5, 6-3, 3-6, 5-7, 4-6 |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Jason Kubler | Loss | 6-3, 3-6, 4-6 |
