Juan Felipe Yanez defeated Rafael Serpa Guinazu 4-6 6-1 6-4 in the Chile F8 round of 32 on clay. The upset overturned the form book — Rafael Serpa Guinazu came in leading the head-to-head 2–1. Juan Felipe Yanez narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-12-04 | Chile F9 | R32 | clay | Juan Felipe Yanez | 6-2 6-4 |
| 1996-11-02 | Uruguay Paraguay Masters 3 | R32 | clay | Rafael Serpa Guinazu | 4-6 7-5 6-2 |
| 1995-07-08 | Colombia Masters 3 | R16 | clay | Rafael Serpa Guinazu | 6-4 6-2 |