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| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Quentin Halys | Win | 6-4, 3-6, 4-6, 6-3, 6-4 |
| Second Round | Daniil Medvedev | Loss | 4-6, 1-6, 2-6 |
| Winston-Salem Open | ||
| Surface: Hard | Date: Aug. 22 - Aug. 28 | Seed: 16 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Marco Cecchinato | Win | 5-7, 6-4, 6-4 |
| Third Round | Pablo Carreno Busta | Loss | 2-6, 3-6 |
| Western & Southern Open | ||
| Surface: Hard | Date: Aug. 15 - Aug. 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jan-Lennard Struff | Win | 7-6 (7-2), 5-7, 6-3 |
| Second Round | Pablo Carreno Busta | Loss | 4-6, 2-6 |
| Hamburg European Open | ||
| Surface: Red Clay | Date: Jul. 12 - Jul. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Maximilian Marterer | Win | 7-6 (7-2), 2-6, 7-6 (7-4) |
| Second Round | Stefanos Tsitsipas | Loss | 6-7 (2-7), 3-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Win | 6-4, 7-6 (7-3), 6-2 |
| Second Round | Soon Woo Kwon | Win | 6-3, 6-7 (8-10), 7-6 (7-2), 5-7, 6-3 |
| Third Round | Roberto Bautista Agut | Loss | 5-7, 1-6, 6-7 (4-7) |
| NOVENTI OPEN | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Zverev | Loss | 4-6, 6-3, 3-6 |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 8 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jurij Rodionov | Loss | 6-2, 3-6, 2-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Mathias Bourgue | Win | 6-3, 6-3, 6-4 |
| Second Round | Taylor Fritz | Win | 6-3, 6-2, 3-6, 6-4 |
| Third Round | Roger Federer | Loss | 6-7 (5-7), 7-6 (7-3), 6-7 (4-7), 5-7 |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 16 - May 22 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Benoit Paire | Win | 6-7 (8-10), 7-6 (7-5), 6-4 |
| Second Round | Feliciano Lopez | Win | 7-5, 6-7 (1-7), 6-3 |
| Quarterfinals | Casper Ruud | Loss | 6-2, 1-6, 4-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Reilly Opelka | Win | 6-4, 6-4 |
| Second Round | Cristian Garin | Loss | 3-6, 4-6 |
| BMW Open by FWU | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Philipp Kohlschreiber | Win | 4-6, 6-4, 6-3 |
| Second Round | Jan-Lennard Struff | Loss | 6-7 (3-7), 7-6 (7-0), 2-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Corentin Moutet | Loss | 5-7, 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marco Cecchinato | Loss | 4-6, 3-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hugo Gaston | Loss | 1-6, 4-6 |
| Abierto Mexicano Telcel presentado por HSBC | ||
| Surface: Hard | Date: Mar. 15 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Gerardo Lopez Villasenor | Win | 6-4, 6-2 |
| Second Round | Milos Raonic | Win | 6-4, 6-2 |
| Quarterfinals | Cameron Norrie | Win | 7-5, 6-4 |
| Semifinals | Alexander Zverev | Loss | 4-6, 6-7 (5-7) |
| Argentina Open | ||
| Surface: Clay | Date: Mar. 1 - Mar. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Thiago Agustin Tirante | Win | 2-6, 6-3, 6-4 |
| Second Round | Albert Ramos-Vinolas | Loss | 5-7, 4-6 |
| Cordoba Open | ||
| Surface: Red Clay | Date: Feb. 22 - Feb. 28 | Seed: 6 |
| Round | Opponent | W / L | Result |
| First Round | Federico Coria | Loss | 1-6, 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Hugo Dellien | Win | 7-5, 6-2, 6-4 |
| Second Round | Dominic Thiem | Loss | 4-6, 0-6, 2-6 |
| Great Ocean Road Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Christopher O'Connell | Loss | 7-5, 4-6, 1-6 |
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