- Tournament: Mutua Madrid Open
- Round: Third Round
- Opponent: Jacob Fearnley
- DOB: 1991-05-16
- Birthplace: Bulgaria
- Height: 75.0 cm
- Weight: 179.0 kg
- Plays: R
- Current World Rank: 16
- Hard: 307-187
- Clay: 103-68
- Grass: 44-34
| Tournament | Date | Sets | Round | Winner | Loser |
|---|---|---|---|---|---|
| Mutua Madrid Open | Apr 26, 2025 | 6-3, 6-4 | Second Round | Grigor Dimitrov | Nicolas Jarry |
| Rolex Monte-Carlo Masters | Apr 11, 2025 | 6-0, 6-0 | Quarter Finals | Alex De Minaur | Grigor Dimitrov |
| Rolex Monte-Carlo Masters | Apr 10, 2025 | 6-3, 3-6, 6-2 | Third Round | Grigor Dimitrov | Alejandro Tabilo |
| Rolex Monte-Carlo Masters | Apr 9, 2025 | 4-6, 6-3, 6-1 | Second Round | Grigor Dimitrov | Valentin Vacherot |
| Rolex Monte-Carlo Masters | Apr 8, 2025 | 6-3, 6-4 | First Round | Grigor Dimitrov | Nicolas Jarry |
| Miami Open presented by Itau | Mar 28, 2025 | 6-2, 6-3 | Semi Finals | Novak Djokovic | Grigor Dimitrov |
| Miami Open presented by Itau | Mar 26, 2025 | 6-7 (6-8), 6-4, 7-6 (7-3) | Quarter Finals | Grigor Dimitrov | Francisco Cerundolo |
| Miami Open presented by Itau | Mar 25, 2025 | 6-4, 7-5 | Fourth Round | Grigor Dimitrov | Brandon Nakashima |
| Miami Open presented by Itau | Mar 23, 2025 | 6-7 (3-7), 6-4, 7-5 | Third Round | Grigor Dimitrov | Karen Khachanov |
| Miami Open presented by Itau | Mar 21, 2025 | 6-1, 6-4 | Second Round | Grigor Dimitrov | Federico Cina |
| Tournament | Date | Sets | Round | Winner | Loser |
|---|---|---|---|---|---|
| Mutua Madrid Open | Apr 28, 2025 | - | Third Round | ||
| Mutua Madrid Open | Apr 26, 2025 | 6-3, 6-4 | Second Round | Grigor Dimitrov | Nicolas Jarry |
| Mutua Madrid Open | Apr 27, 2024 | 6-2, 6-7 (4-7), 6-3 | Second Round | Jakub Mensik | Grigor Dimitrov |
| Mutua Madrid Open | Apr 30, 2023 | 6-2, 7-5 | Third Round | Carlos Alcaraz | Grigor Dimitrov |
| Mutua Madrid Open | Apr 28, 2023 | 7-6 (8-6), 7-6 (7-2) | Second Round | Grigor Dimitrov | Gregoire Barrere |
| Mutua Madrid Open | May 8, 2014 | 3-6, 6-3, 6-2 | Third Round | Tomas Berdych | Grigor Dimitrov |
| Mutua Madrid Open | May 7, 2014 | 4-6, 6-3, 7-6 (9-7) | Second Round | Grigor Dimitrov | Marius Copil |
| Mutua Madrid Open | May 5, 2014 | 6-2, 6-4 | First Round | Grigor Dimitrov | Pablo Carreno Busta |
| Mutua Madrid Open | May 9, 2013 | 3-6, 6-4, 6-1 | Third Round | Stanislas Wawrinka | Grigor Dimitrov |
| Mutua Madrid Open | May 7, 2013 | 7-6 (8-6), 6-7 (8-10), 6-3 | Second Round | Grigor Dimitrov | Novak Djokovic |
