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| US Open | ||
| Surface: Hard | Date: Aug. 30 - Sep. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Matteo Berrettini | Loss | 6-7 (5-7), 6-7 (7-9), 3-6 |
| Wimbledon | ||
| Surface: Grass | Date: Jun. 28 - Jul. 11 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Aslan Karatsev | Win | 7-6 (7-4), 7-6 (8-6), 6-3 |
| Second Round | Ilya Ivashka | Loss | 6-4, 3-6, 2-6, 4-6 |
| cinch Championships | ||
| Surface: Grass | Date: Jun. 14 - Jun. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Bublik | Loss | 4-6, 6-3, 3-6 |
| MercedesCup | ||
| Surface: Grass | Date: Jun. 8 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Yannick Hanfmann | Loss | 4-6, 4-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 30 - Jun. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Stefanos Tsitsipas | Loss | 6-7 (6-8), 3-6, 1-6 |
| Serbia Open | ||
| Surface: Red Clay | Date: May 16 - May 29 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Tennys Sandgren | Win | 6-4, 6-2 |
| Second Round | Dusan Lajovic | Loss | 3-6, 4-6 |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 29 - May 9 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Loss | 6-7 (6-8), 7-6 (9-7), 2-6 |
| Millennium Estoril Open | ||
| Surface: Red Clay | Date: Apr. 26 - May 2 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Jaume Munar | Win | 3-6, 6-3, 6-4 |
| Second Round | Alejandro Davidovich Fokina | Loss | 1-6, 2-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 19 - Apr. 25 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nikoloz Basilashvili | Win | 6-4, 3-6, 6-3 |
| Second Round | Denis Shapovalov | Loss | 3-6, 5-7 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 11 - Apr. 18 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexander Bublik | Win | 6-4, 0-6, 7-5 |
| Second Round | Grigor Dimitrov | Loss | 6-7 (3-7), 4-6 |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 23 - Apr. 4 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Kudla | Loss | 6-3, 3-6, 4-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Mar. 14 - Mar. 20 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Albert Ramos-Vinolas | Win | 6-3, 3-6, 6-4 |
| Second Round | Alex De Minaur | Win | 2-6, 6-3, 6-4 |
| Third Round | Karen Khachanov | Win | 6-7 (3-7), 6-4, 6-4 |
| Quarterfinals | Denis Shapovalov | Loss | 5-7, 4-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Mar. 8 - Mar. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Loss | 4-6, 6-1, 2-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Mar. 1 - Mar. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Ugo Humbert | Win | 4-6, 7-6 (7-5), 7-6 (7-4) |
| Second Round | David Goffin | Win | 7-6 (7-3), 7-6 (7-5) |
| Quarterfinals | Andrey Rublev | Loss | 6-7 (2-7), 7-6 (7-2), 4-6 |
| Australian Open | ||
| Surface: Hard | Date: Feb. 8 - Feb. 21 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Novak Djokovic | Loss | 3-6, 1-6, 2-6 |
| Murray River Open | ||
| Surface: Hard | Date: Feb. 1 - Feb. 7 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Marin Cilic | Win | 2-6, 6-3, 7-6 (10-8) |
| Second Round | Gilles Simon | Win | 6-3, 6-4 |
| Third Round | Taylor Fritz | Win | 6-2, 6-4 |
| Quarterfinals | Stan Wawrinka | Win | Retired |
| Semifinals | Daniel Evans | Loss | 2-6, 2-6 |
| Antalya Open | ||
| Surface: Grass | Date: Jan. 7 - Jan. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Radu Albot | Win | 6-3, 6-4 |
| Second Round | Fabio Fognini | Win | 7-6 (7-4), 6-7 (1-7), 7-6 (7-5) |
| Quarterfinals | Jan-Lennard Struff | Win | 4-6, 6-2, 7-6 (10-8) |
| Semifinals | Alexander Bublik | Loss | 4-6, 7-6 (7-4), 3-6 |
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