Grigor Dimitrov (Bulgaria) 3 - 1 Christopher O'Connell (Australia)
| Date | Tournament | Rnd | Winner | Score |
|---|---|---|---|---|
| 25 Feb 2025 |
Dubai Duty Free Championships
Dubai,
United Arab Emirates
ATP Tour 500, Hard |
R32 |
Christopher O'Connell
(AUS  )
|
0-6 ret. |
| 24 Sep 2023 |
Chengdu Open
Chengdu,
China
ATP Tour 250, Hard |
Q |
Grigor Dimitrov
(BUL  )
|
6-4 6-1 |
| 25 May 2023 |
Gonet Geneva Open
Geneva,
Switzerland
ATP Tour 250, Clay |
Q |
Grigor Dimitrov
(BUL )
|
6-7(5) 7-5 6-4 |
| 17 Jan 2017 |
Australian Open
Melbourne,
Australia
Grand Slam, Hard |
R128 |
Grigor Dimitrov
(BUL )
|
7-6(2) 6-3 6-3 |