Sandra Cacic defeated Diana Ospina 7-6 6-0 in the Boca Raton 10K round of 32 on hard. The upset overturned the form book — Diana Ospina came in leading the head-to-head 1–0. Sandra Cacic claimed a first win over Diana Ospina in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Albuquerque 50K | R32 | hard | Diana Ospina | 6-4 7-6 |