Jennifer Hopkins defeated Jolene Watanabe 7-6 7-6 in the Lexington 50K round of 16 on hard. Jennifer Hopkins extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-01-31 | Clearwater 25K | QF | hard | Jolene Watanabe | 6-1 4-6 6-2 |
| 1999-10-04 | Albuquerque 50K | R16 | hard | Jennifer Hopkins | 3-6 6-2 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.