Level, 1 wins each over 2 singles meetings since 2025. Last meeting on 20/09/2026 at Plovdiv 4 Challenger.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 20/09/2026 | Plovdiv 4 Challenger | Qualifying 1 | clay | Obradovic | 7-6(5) 6-4 |
| 10/08/2025 | Sofia 1 Challenger | Qualifying 1 | clay | Andreescu | 3-6 2-6 |
| clay | Obradovic 1 - 1 Andreescu |
| 2026 | Obradovic 1 - 0 Andreescu |
| 2025 | Obradovic 0 - 1 Andreescu |
182 wins, 133 losses since 2021 (57.8%).
Last matches: D V D V D
185 wins, 103 losses since 2021 (64.2%).
Last matches: D D V V V
Level, 1 wins each over 2 singles meetings since 2025.
On 20/09/2026, at Plovdiv 4 Challenger (Qualifying 1): Dusan Obradovic won 7-6(5) 6-4.