Pamela Montez defeated Belinda Woolcock 1-6 6-3 7-5 in the W25 Osprey round of 32 on clay. The upset overturned the form book — Belinda Woolcock came in leading the head-to-head 1–0. Pamela Montez claimed a first win over Belinda Woolcock in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2019-06-04 | W25 Bethany Beach | R32 | clay | Belinda Woolcock | 6-0 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.