Rafael Serpa Guinazu defeated Juan Felipe Yanez 4-6 7-5 6-2 in the Uruguay Paraguay Masters 3 round of 32 on clay. Rafael Serpa Guinazu extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-27 | Chile F8 | R32 | clay | Juan Felipe Yanez | 4-6 6-1 6-4 |
| 1995-07-08 | Colombia Masters 3 | R16 | clay | Rafael Serpa Guinazu | 6-4 6-2 |