| ||||||||||||||
| BOSS OPEN | ||
| Surface: Grass | Date: Jun. 6 - Jun. 12 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Nick Kyrgios | Loss | 6-7 (3-7), 3-6 |
| Roland Garros | ||
| Surface: Red Clay | Date: May 22 - Jun. 5 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Goffin | Loss | 4-6, 6-4, 4-6, 4-6 |
| BMW Open by American Express | ||
| Surface: Red Clay | Date: Apr. 25 - May 1 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Holger Rune | Loss | 6-7 (4-7), 3-6 |
| Serbia Open | ||
| Surface: Red Clay | Date: Apr. 18 - Apr. 24 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Henri Laaksonen | Win | 6-2, 7-5 |
| Second Round | Andrey Rublev | Loss | 6-4, 6-7 (1-7), 2-6 |
| Rolex Monte-Carlo Masters | ||
| Surface: Clay | Date: Apr. 10 - Apr. 17 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | David Goffin | Loss | 4-6, 3-6 |
| Grand Prix Hassan II | ||
| Surface: Red Clay | Date: Apr. 4 - Apr. 10 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Laslo Djere | Loss | 4-6, 4-6 |
| ABN AMRO World Tennis Tournament | ||
| Surface: Hard | Date: Feb. 7 - Feb. 13 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Denis Shapovalov | Win | 6-4, 6-4 |
| Second Round | Botic van de Zandschulp | Win | 1-6, 6-4, 6-4 |
| Quarterfinals | Lorenzo Musetti | Win | 6-3, 1-6, 7-5 |
| Semifinals | Stefanos Tsitsipas | Loss | 6-4, 4-6, 2-6 |
| Australian Open | ||
| Surface: Hard | Date: Jan. 17 - Jan. 30 | Seed: None |
| Round | Opponent | W / L | Result |
| First Round | Grigor Dimitrov | Loss | 4-6, 6-4, 3-6, 5-7 |
