Holly Parkinson defeated Jill Craybas 6-0 6-3 in the Santa Clara 75K round of 32 on hard. The upset overturned the form book — Jill Craybas came in leading the head-to-head 3–0, but Holly Parkinson had been the form player, winning 3 of their last 4 on hard. Holly Parkinson claimed a first win over Jill Craybas in four meetings, narrowing 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 |
| 2000-04-24 | Sarasota 75K | R32 | clay | Jill Craybas | 6-3 3-6 7-6(3) |
| 2000-01-03 | Auckland | QF | hard | Jill Craybas | 6-1 5-7 7-6(3) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.