Daniel Caracciolo defeated Mariano Delfino 6-2 6-1 in the Uruguay Masters 4 round of 32 on clay. The upset overturned the form book — Mariano Delfino came in leading the head-to-head 1–0, but Daniel Caracciolo had been the form player, winning 6 of their last 10 on clay. Daniel Caracciolo claimed a first win over Mariano Delfino in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-08 | Argentina F5 | R16 | clay | Mariano Delfino | 6-4 0-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.