Lilia Osterloh defeated Jill Craybas 0-6 6-3 6-1 in the Montreal round of 64 on hard. The upset overturned the form book — Jill Craybas came in leading the head-to-head 3–2. Lilia Osterloh narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-10-29 | Quebec City | R32 | hard | Jill Craybas | 6-4 2-6 6-2 |
| 2007-07-23 | Stanford | R32 | hard | Lilia Osterloh | 6-2 7-5 |
| 2006-02-20 | Memphis | QF | hard | Jill Craybas | 6-4 6-1 |
| 2002-04-15 | Charleston | R64 | clay | Jill Craybas | 6-2 6-0 |
| 2001-02-19 | Oklahoma City | R32 | carpet | Lilia Osterloh | 7-6(2) 6-4 |
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 (52 vs 200). ATP, WTA & Challenger.