Blaz Trupej defeated Rodrigo Ribeiro 3-6 6-4 6-4 in the Slovenia F2 round of 16 on clay. The upset overturned the form book — Rodrigo Ribeiro came in leading the head-to-head 1–0, but Blaz Trupej had been the form player, winning 2 of their last 8 on clay. Blaz Trupej claimed a first win over Rodrigo Ribeiro in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-26 | Slovenia F3 | R32 | clay | Rodrigo Ribeiro | 7-5 4-6 6-2 |