Rodrigo Monte defeated Cristian Villagran 6-1 6-4 in the Jamaica F1 round of 16 on hard. The result followed the form book — Rodrigo Monte came in leading the head-to-head 1–0. Rodrigo Monte extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-11 | Paraguay F1 | R32 | clay | Rodrigo Monte | 6-4 2-6 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.