Ashley Harkleroad defeated Jill Craybas 6-2 6-3 in the San Diego round of 64 on hard. The upset overturned the form book — Jill Craybas came in leading the head-to-head 3–0, defending last year's round of 64. Ashley Harkleroad claimed a first win over Jill Craybas in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-01-02 | Auckland | R32 | hard | Jill Craybas | 2-6 6-1 7-6(4) |
| 2005-06-20 | Wimbledon | R128 | grass | Jill Craybas | 6-4 4-6 6-4 |
| 2004-03-24 | Miami | R128 | hard | Jill Craybas | 6-2 3-0 RET |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (56 vs 196). ATP, WTA & Challenger.