- Tournament: N/A
- Round: N/A
- Opponent: N/A
- DOB: 1991-05-16
- Birthplace: Bulgaria
- Height: 75.0 cm
- Weight: 179.0 kg
- Plays: R
- Current World Rank: 10
- Hard: 285-174
- Clay: 93-64
- Grass: 40-32
| Tournament | Date | Sets | Round | Winner | Loser |
|---|---|---|---|---|---|
| Rolex Monte-Carlo Masters | Apr 11, 2024 | 7-6 (11-9), 3-6, 7-6 (7-2) | Third Round | Holger Rune | Grigor Dimitrov |
| Rolex Monte-Carlo Masters | Apr 11, 2024 | 6-4, 6-3 | Second Round | Grigor Dimitrov | Miomir Kecmanovic |
| Rolex Monte-Carlo Masters | Apr 8, 2024 | 7-5, 6-2 | First Round | Grigor Dimitrov | Valentin Vacherot |
| Miami Open presented by Itau | Mar 31, 2024 | 6-3, 6-1 | Finals | Jannik Sinner | Grigor Dimitrov |
| Miami Open presented by Itau | Mar 29, 2024 | 6-4, 6-7 (4-7), 6-4 | Semi Finals | Grigor Dimitrov | Alexander Zverev |
| Miami Open presented by Itau | Mar 28, 2024 | 6-2, 6-4 | Quarter Finals | Grigor Dimitrov | Carlos Alcaraz |
| Miami Open presented by Itau | Mar 26, 2024 | 3-6, 6-3, 7-6 (7-3) | Fourth Round | Grigor Dimitrov | Hubert Hurkacz |
| Miami Open presented by Itau | Mar 25, 2024 | 6-1, 6-0 | Third Round | Grigor Dimitrov | Yannick Hanfmann |
| Miami Open presented by Itau | Mar 24, 2024 | 6-7 (5-7), 7-6 (7-5), 6-2 | Second Round | Grigor Dimitrov | Alejandro Tabilo |
| BNP Paribas Open | Mar 13, 2024 | 6-4, 6-4 | Fourth Round | Daniil Medvedev | Grigor Dimitrov |
| Tournament | Date | Sets | Round | Winner | Loser |
|---|---|---|---|---|---|
| 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 |
| Mutua Madrid Open | May 6, 2013 | 6-2, 6-4 | First Round | Grigor Dimitrov | Javier Marti |
