Jill Craybas defeated Holly Parkinson 6-3 3-6 7-6 in the Sarasota 75K round of 32 on clay. The result followed the form book — Jill Craybas came in leading the head-to-head 2–1. Jill Craybas extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-23 | Dallas 50K | R16 | hard | Jill Craybas | 6-2 6-4 |
| 2000-01-03 | Auckland | QF | hard | Jill Craybas | 6-1 5-7 7-6(3) |
| 1999-09-27 | Santa Clara 75K | R32 | hard | Holly Parkinson | 6-0 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.