Jill Craybas defeated Karin Miller 6-4 6-3 in the Rockford IL 25K round of 32 on hard. The result followed the form book — Jill Craybas came in leading the head-to-head 4–0. Jill Craybas extended the head-to-head to 5–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-27 | Tucson Challenger | R32 | hard | Jill Craybas | 6-1 4-6 6-0 |
| 2000-07-17 | Mahwah 50K | R16 | hard | Jill Craybas | 3-6 6-3 6-4 |
| 2000-05-01 | Virginia Beach 25K | R32 | clay | Jill Craybas | 6-7(5) 6-3 6-1 |
| 1999-07-26 | Salt Lake City 50K | R16 | hard | Jill Craybas | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.