Alain Lemaitre defeated Marco Osorio 4-6 6-2 6-3 in the Mexico 3 Masters 1 round of 32 on hard. The upset overturned the form book — Marco Osorio came in leading the head-to-head 3–1. Alain Lemaitre narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Mexico F7 | R16 | hard | Marco Osorio | 6-0 6-1 |
| 1996-04-13 | Mexico 2 Masters 3 | QF | hard | Alain Lemaitre | 7-6 7-6 |
| 1996-04-13 | Mexico 2 Masters 4 | R32 | hard | Marco Osorio | 2-6 6-4 6-2 |
| 1995-04-22 | Mexico 2 Masters 1 | QF | clay | Marco Osorio | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.