Rodrigo Monte defeated Rodrigo Ribeiro 6-0 3-6 6-1 in the Bolivia F2 round of 32 on clay. The upset overturned the form book — Rodrigo Ribeiro came in leading the head-to-head 1–0, but Rodrigo Monte had been the form player, winning 3 of their last 8 on clay. Rodrigo Monte claimed a first win over Rodrigo Ribeiro in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-01 | Portugal 1 1 | QF | clay | Rodrigo Ribeiro | 2-6 6-4 6-0 |