Jose De Armas defeated Miguel Gallardo Valles 6-3 6-2 6-2 in the VEN vs MEX round robin on hard. Jose De Armas extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Mexico F5 | R32 | hard | Jose De Armas | 6-1 7-6 |
| 1999-07-24 | Mexico 1 Masters 1 | SF | hard | Miguel Gallardo Valles | 7-6 6-4 |