Rachel Mcquillan defeated Jennifer Hopkins 6-4 6-4 in the Nurioopta 25K round of 32 on hard. The upset overturned the form book — Jennifer Hopkins came in leading the head-to-head 4–0. Rachel Mcquillan claimed a first win over Jennifer Hopkins in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-31 | Lexington 50K | QF | hard | Jennifer Hopkins | 6-3 7-5 |
| 2000-05-29 | Roland Garros | Q32 | clay | Jennifer Hopkins | 1-6 7-5 6-2 |
| 2000-04-24 | Sarasota 75K | R32 | clay | Jennifer Hopkins | 6-2 6-3 |
| 1999-11-15 | Mount Gambier 25K | QF | hard | Jennifer Hopkins | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.