Paulo Taicher defeated Chris Groer 4-6 6-4 6-4 in the Central America Masters 3 round of 32 on clay. The upset overturned the form book — Chris Groer came in leading the head-to-head 1–0. Paulo Taicher claimed a first win over Chris Groer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-23 | Central America Masters 4 | R16 | clay | Chris Groer | 6-4 6-4 |