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| Erste Bank Open 500 | ||
| Surface: Hard | Date: Oct. 25 - Oct. 31 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Carlos Alcaraz | Loss | 4-6, 3-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Oct. 6 - Oct. 17 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Kei Nishikori | Win | 4-6, 6-3, 6-4 |
| Third Round | Diego Schwartzman | Loss | 7-5, 4-6, 0-6 |
| San Diego Open | ||
| Surface: Hard | Date: Sep. 27 - Oct. 3 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Kevin Anderson | Win | 7-6 (13-11), 7-5 |
| Second Round | Cameron Norrie | Loss | 6-7 (3-7), 3-6 |
| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: 24 |
| Round | Opponent | W / L | Result |
| First Round | Thiago Monteiro | Win | 6-3, 6-7 (6-8), 6-4, 6-1 |
| Second Round | Marcos Giron | Win | 6-4, 7-6 (7-3), 2-6, 6-3 |
| Third Round | Alexei Popyrin | Win | 4-6, 3-6, 6-3, 6-4, 7-6 (7-1) |
| Fourth Round | Daniil Medvedev | Loss | 3-6, 4-6, 3-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 28 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Lucas Pouille | Win | 3-6, 6-4, 6-1 |
| Third Round | Richard Gasquet | Loss | 4-6, 6-7 (4-7) |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Diego Schwartzman | Loss | 2-6, 6-4, 3-6 |
| Open de la Banque Nationale presentee par Rogers | ||
| Surface: Hard | Date: Aug. 9 - Aug. 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Bublik | Loss | 4-6, 4-6 |
| Citi Open | ||
| Surface: Hard | Date: Aug. 2 - Aug. 8 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Brandon Nakashima | Loss | 6-7 (1-7), 0-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Feliciano Lopez | Win | 7-6 (7-4), 6-2, 7-5 |
| Second Round | Dusan Lajovic | Win | 6-3, 6-3, 6-4 |
| Third Round | Sebastian Korda | Loss | 3-6, 6-3, 3-6, 4-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Win | 6-4, 6-4 |
| Second Round | Adrian Mannarino | Win | 6-4, 7-6 (9-7) |
| Quarterfinals | Matteo Berrettini | Loss | 6-7 (5-7), 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: 25 |
| Round | Opponent | W / L | Result |
| First Round | Miomir Kecmanovic | Loss | 6-1, 3-6, 3-6, 4-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 9 - May 16 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Taylor Fritz | Loss | 3-6, 2-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jeremy Chardy | Win | 7-6 (8-6), 6-7 (7-9), 6-2 |
| Second Round | John Millman | Win | 6-7 (5-7), 6-2, 6-3 |
| Third Round | Alexander Zverev | Loss | 3-6, 6-7 (3-7) |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Corentin Moutet | Loss | 4-6, 7-5, 3-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Dusan Lajovic | Win | 6-3, 6-7 (11-13), 6-2 |
| Second Round | Hubert Hurkacz | Win | 6-4, 6-1 |
| Third Round | Novak Djokovic | Win | 6-4, 7-5 |
| Quarterfinals | David Goffin | Win | 5-7, 6-3, 6-4 |
| Semifinals | Stefanos Tsitsipas | Loss | 2-6, 1-6 |
| Sardegna Open | ||
| Surface: Red Clay | Date: Apr. 5 - Apr. 11 | Seed: 1 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Lorenzo Musetti | Loss | 1-6, 6-1, 6-7 (8-10) |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: 19 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Frances Tiafoe | Loss | 7-6 (7-5), 3-6, 3-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Mar. 14 - Mar. 20 | Seed: 12 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Aslan Karatsev | Loss | 4-6, 6-4, 4-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jeremy Chardy | Win | 6-4, 1-6, 6-2 |
| Second Round | Roger Federer | Loss | 6-7 (8-10), 6-3, 5-7 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: 30 |
| Round | Opponent | W / L | Result |
| First Round | Cameron Norrie | Loss | 4-6, 6-4, 4-6, 5-7 |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Pedro Sousa | Win | 6-3, 7-5 |
| Third Round | Marcos Giron | Win | 6-4, 7-6 (7-4) |
| Quarterfinals | Borna Coric | Win | 7-5, 7-6 (7-1) |
| Semifinals | Jeremy Chardy | Win | 6-2, 6-2 |
| Final | Felix Auger-Aliassime | Win | 6-2, 6-3 |
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