Dimo Tolev defeated Josef Nesticky 7-6 1-6 7-6 in the Bulgaria Masters 2 round of 32 on clay. The upset overturned the form book — Josef Nesticky came in leading the head-to-head 1–0. Dimo Tolev claimed a first win over Josef Nesticky in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Bulgaria 1 2 | R32 | clay | Josef Nesticky | 6-4 7-6(4) |