Martin Vassallo Arguello defeated Rodolfo Rake 6-3 6-1 in the Chile F2 round of 32 on clay. The upset overturned the form book — Rodolfo Rake came in leading the head-to-head 2–0. Martin Vassallo Arguello claimed a first win over Rodolfo Rake in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Bolivia F3 | R16 | clay | Rodolfo Rake | 6-2 6-4 |
| 1998-09-07 | Peru F2 | R16 | clay | Rodolfo Rake | 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.