Matej Pampoulov defeated Ivo Bratanov 5-7 6-3 7-5 in the Greece 3 Masters 2 round of 32 on carpet. The upset overturned the form book — Ivo Bratanov came in leading the head-to-head 1–0. Matej Pampoulov claimed a first win over Ivo Bratanov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-08 | Bulgaria 1 4 | R16 | clay | Ivo Bratanov | 6-3 4-6 6-4 |