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| Terra Wortmann Open | ||
| Surface: Grass | Date: Jun. 13 - Jun. 19 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Andrey Rublev | Win | 7-6 (7-1), 6-4 |
| Second Round | Oscar Otte | Loss | 6-4, 0-6, 6-7 (3-7) |
| BOSS OPEN | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Lorenzo Musetti | Win | 7-5, 6-3 |
| Second Round | Nick Kyrgios | Loss | 7-6 (7-4), 4-6, 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: 22 |
| Round | Opponent | W / L | Result |
| First Round | Maxime Cressy | Win | 3-6, 2-6, 7-6 (10-8), 6-4, 6-4 |
| Second Round | Mackenzie McDonald | Loss | 3-6, 1-6, 4-6 |
| Gonet Geneva Open | ||
| Surface: Clay | Date: May 15 - May 21 | Seed: 5 |
| Round | Opponent | W / L | Result |
| First Round | Facundo Bagnis | Win | 6-4, 0-0 Retired |
| Second Round | Joao Sousa | Loss | 4-6, 3-6 |
| Internazionali BNL d'Italia | ||
| Surface: Red Clay | Date: May 8 - May 15 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Daniel Evans | Win | 7-6 (7-2), 6-2 |
| Second Round | Denis Shapovalov | Loss | 4-6, 6-7 (5-7) |
| Mutua Madrid Open | ||
| Surface: Hard | Date: Apr. 28 - May 8 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Fabio Fognini | Win | 7-5, 6-4 |
| Second Round | Carlos Alcaraz | Loss | 3-6, 5-7 |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Ilya Ivashka | Win | 3-6, 6-2, 6-4 |
| Quarterfinals | Miomir Kecmanovic | Loss | 6-7 (5-7), 2-6 |
| Barcelona Open Banc Sabadell | ||
| Surface: Clay | Date: Apr. 18 - Apr. 24 | Seed: 9 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jaume Munar | Loss | 1-6, 4-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: 15 |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 3-6, 0-2 Retired |
| Miami Open presented by Itau | ||
| Surface: Hard | Date: Mar. 22 - Apr. 3 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Jenson Brooksby | Loss | 3-6, 1-6 |
| BNP Paribas Open | ||
| Surface: Hard | Date: Mar. 9 - Mar. 20 | Seed: 18 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Fabio Fognini | Win | Retired |
| Third Round | Cameron Norrie | Loss | 6-3, 3-6, 1-6 |
| Dubai Duty Free Tennis Championships | ||
| Surface: Hard | Date: Feb. 21 - Feb. 26 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Alexei Popyrin | Loss | 2-6, 3-6 |
| Qatar ExxonMobil Open | ||
| Surface: Hard | Date: Feb. 14 - Feb. 19 | Seed: 3 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Elias Ymer | Win | 6-4, 7-5 |
| Quarterfinals | Marton Fucsovics | Win | 1-6, 6-3, 7-5 |
| Semifinals | Arthur Rinderknech | Win | 6-4, 6-2 |
| Final | Roberto Bautista Agut | Loss | 3-6, 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: 8 |
| Round | Opponent | W / L | Result |
| First Round | Mackenzie McDonald | Loss | 3-6, 2-6 |
| Open Sud de France | ||
| Surface: Hard | Date: Jan. 31 - Feb. 6 | Seed: 4 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Damir Dzumhur | Loss | 1-6, 7-5, 2-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: 21 |
| Round | Opponent | W / L | Result |
| First Round | Andy Murray | Loss | 1-6, 6-3, 4-6, 7-6 (7-5), 4-6 |
| Sydney Tennis Classic | ||
| Surface: Hard | Date: Jan. 10 - Jan. 15 | Seed: 2 |
| Round | Opponent | W / L | Result |
| First Round | Bye | ||
| Second Round | Andy Murray | Loss | 7-6 (7-4), 6-7 (3-7), 3-6 |
