Rossana De Los Rios defeated Diana Ospina 7-6 6-2 in the San Francisco CA 50K round of 16 on hard. The upset overturned the form book — Diana Ospina came in leading the head-to-head 1–0. Rossana De Los Rios claimed a first win over Diana Ospina in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-06-07 | Allentown PA 25K | SF | hard | Diana Ospina | 3-6 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.