Catalina Castano defeated Holly Parkinson 6-3 5-7 7-6 in the Cali 25K qualifying round on clay. The upset overturned the form book — Holly Parkinson came in leading the head-to-head 2–0. Catalina Castano claimed a first win over Holly Parkinson in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Easton 10K | QF | hard | Holly Parkinson | 7-5 3-6 7-6 |
| 1999-06-14 | Mount Pleasant 25K | R16 | hard | Holly Parkinson | 6-0 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.