Yoannis Montesino defeated Robyn Mawdsley 6-4 6-3 in the Tuxtla Gutierrez 3 5K round of 32 on hard. The upset overturned the form book — Robyn Mawdsley came in leading the head-to-head 1–0. Yoannis Montesino claimed a first win over Robyn Mawdsley in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-03-11 | Tuxtla Gutierrez 2 5K | R16 | hard | Robyn Mawdsley | 6-3 6-4 |