Daniel Caracciolo defeated Martin Vassallo Arguello 3-6 6-3 6-3 in the Chile F5 round of 32 on clay. The upset overturned the form book — Martin Vassallo Arguello came in leading the head-to-head 2–0. Daniel Caracciolo claimed a first win over Martin Vassallo Arguello in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-07-30 | Argentina F7 | SF | clay | Martin Vassallo Arguello | 6-4 6-3 |
| 2001-03-12 | Argentina F1 | R32 | clay | Martin Vassallo Arguello | 1-6 7-6(4) 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.