Shelley Bryce defeated Dragana Ilic 6-3 6-3 in the Bucharest 25K round of 32 on clay. The upset overturned the form book — Dragana Ilic came in leading the head-to-head 1–0. Shelley Bryce claimed a first win over Dragana Ilic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | Kastoria 10K | F | carpet | Dragana Ilic | 6-4 6-4 |