Anna Gerasimou advanced when Nadejda Vassileva retired 3-2 in the Haskovo 10K semi-final. Anna Gerasimou claimed a first win over Nadejda Vassileva in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-06-19 | Bucharest 3 10K | SF | clay | Nadejda Vassileva | 4-1 |
| 2002-09-23 | Volos 10K | R32 | carpet | Nadejda Vassileva | 1-6 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.