Miguel Gallardo Valles defeated Colin Bennett 6-4 7-6 in the Mexico 1 Masters 1 qualifying round on hard. The upset overturned the form book — Colin Bennett came in leading the head-to-head 1–0, but Miguel Gallardo Valles had been the form player, winning 4 of their last 6 on hard. Miguel Gallardo Valles claimed a first win over Colin Bennett in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-24 | Mexico 1 Masters 2 | R32 | hard | Colin Bennett | 5-7 7-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.