Alexandra Osborne defeated Andrea Renee Villarreal 4-6 6-4 6-1 in the W25 Evansville round of 32 on hard. The upset overturned the form book — Andrea Renee Villarreal came in leading the head-to-head 2–0. Alexandra Osborne claimed a first win over Andrea Renee Villarreal in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-07-31 | W25 Fort Worth | R32 | hard | Andrea Renee Villarreal | 6-3 6-7(7) 6-3 |
| 2019-04-26 | W15 Cancun 6 | QF | hard | Andrea Renee Villarreal | 6-2 4-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.