Dragana Ilic defeated Katarina Misic 7-6 6-2 6-3 in the Sofia 10K round of 16 on clay. The upset overturned the form book — Katarina Misic came in leading the head-to-head 2–1. Dragana Ilic narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-11 | Rhodes 25K | R32 | clay | Katarina Misic | 6-2 6-4 |
| 1998-09-01 | Xanthi 10K | R16 | hard | Katarina Misic | 6-3 2-6 6-4 |
| 1998-06-23 | Kavala 10K | SF | hard | Dragana Ilic | 7-6 7-5 |