Level, 1 wins each over 2 singles meetings since 2021. Last meeting on 14/04/2022 at Monte-Carlo Rolex Masters - Monte-Carlo.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 14/04/2022 | Monte-Carlo Rolex Masters - Monte-Carlo | Round 3 | clay | Dimitrov | 3-6 5-7 |
| 03/10/2021 | San Diego Open - San Diego | Semi-final | hard | Ruud | 4-6 6-4 4-6 |
| clay | Dimitrov 1 - 0 Ruud |
| hard | Dimitrov 0 - 1 Ruud |
| 2022 | Dimitrov 1 - 0 Ruud |
| 2021 | Dimitrov 0 - 1 Ruud |
161 wins, 103 losses since 2021 (61.0%).
Last matches: D V V V D
243 wins, 117 losses since 2021 (67.5%).
Last matches: D D V D V
Level, 1 wins each over 2 singles meetings since 2021.
On 14/04/2022, at Monte-Carlo Rolex Masters - Monte-Carlo (Round 3): Grigor Dimitrov won 3-6 5-7.