Grigor Dimitrov leads 2 to 1 over 3 singles meetings since 2023. Last meeting on 25/02/2025 at Dubai Duty Free Tennis Championships - Dubai.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 25/02/2025 | Dubai Duty Free Tennis Championships - Dubai | Round 1 | hard | O'Connell | 5-0 |
| 24/09/2023 | Chengdu Open - Chengdu | Quarter-final | hard | Dimitrov | 6-4 6-1 |
| 25/05/2023 | Gonet Geneva Open - Geneva | Quarter-final | clay | Dimitrov | 7-6(5) 5-7 3-5 |
| hard | Dimitrov 1 - 1 O'Connell |
| clay | Dimitrov 1 - 0 O'Connell |
| 2025 | Dimitrov 0 - 1 O'Connell |
| 2023 | Dimitrov 2 - 0 O'Connell |
161 wins, 103 losses since 2021 (61.0%).
Last matches: D V V V D
180 wins, 145 losses since 2021 (55.4%).
Last matches: D V V D V
Grigor Dimitrov leads 2 to 1 over 3 singles meetings since 2023.
On 25/02/2025, at Dubai Duty Free Tennis Championships - Dubai (Round 1): Christopher O'Connell won 5-0.