Ansley Cargill advanced when Olga Puchkova retired 1-0 in the St Paul MN 50K qualifying round. Ansley Cargill extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-10-10 | San Francisco CA 50K | R32 | hard | Ansley Cargill | 6-1 5-7 7-5 |
| 2003-10-13 | Sedona AZ 50K | R16 | hard | Ansley Cargill | 7-5 4-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.