Rodrigo Ribeiro defeated Rodrigo Monte 2-6 6-4 6-0 in the Portugal 1 1 qualifying round on clay. The upset overturned the form book — Rodrigo Monte came in leading the head-to-head 1–0. Rodrigo Ribeiro claimed a first win over Rodrigo Monte in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-09-28 | Bolivia F2 | R32 | clay | Rodrigo Monte | 6-0 3-6 6-1 |