Josef Nesticky defeated Dimo Tolev 6-4 7-6 in the Bulgaria 1 2 round of 32 on clay. The upset overturned the form book — Dimo Tolev came in leading the head-to-head 1–0. Josef Nesticky claimed a first win over Dimo Tolev in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-24 | Bulgaria Masters 2 | R32 | clay | Dimo Tolev | 7-6 1-6 7-6 |