Monte-Carlo, Monaco, 
)
Madrid, Spain, 
1Grigor Dimitrov (Bulgaria) 3 - 1 Aslan Karatsev (___)
| Date | Tournament | Surface | Rd | Opp. Rank |
Winner | Score |
|---|---|---|---|---|---|---|
| 13 Feb 2023 |
ABN Amro Rotterdam, The Netherlands ATP Tour 500 |
R32 | Grigor Dimitrov (BUL) | 6-1 6-3 | ||
| 17 Jan 2023 |
Australian Open Melbourne, Australia Grand Slam |
R128 | Grigor Dimitrov (BUL) | 7-6(3) 7-5 6-2 | ||
| 01 Oct 2021 |
San Diego Open San Diego, CA, USA ATP Tour 250 |
Q | Grigor Dimitrov (BUL) | 6-1 1-6 6-2 | ||
| 16 Feb 2021 |
Australian Open Melbourne, Australia Grand Slam |
Q | Aslan Karatsev (___) | 6-2 4-6 1-6 2-6 |