Jose De Armas defeated Miguel Gallardo Valles 6-1 7-6 in the Mexico F5 round of 32 on hard. Jose De Armas extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-07-10 | Davis Cup G2 R2: VEN vs MEX | RR | hard | Jose De Armas | 6-3 6-2 6-2 |
| 1999-07-24 | Mexico 1 Masters 1 | SF | hard | Miguel Gallardo Valles | 7-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.