Jorgelina Torti defeated Natalia Gussoni 7-6 6-3 in the Santiago 10K qualifying round on clay. The upset overturned the form book — Natalia Gussoni came in leading the head-to-head 2–0, but Jorgelina Torti had been the form player, winning 4 of their last 8 on clay. Jorgelina Torti claimed a first win over Natalia Gussoni in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Montevideo 10K | R16 | clay | Natalia Gussoni | 3-6 6-3 6-2 |
| 1999-05-10 | Tortosa 10K | R16 | clay | Natalia Gussoni | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.