Jill Craybas defeated Rossana De Los Rios 6-3 6-3 in the Bastad round of 32 on clay. The result followed the form book — Jill Craybas came in defending last year's round of 32. Jill Craybas extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-11 | Rome | Q32 | clay | Jill Craybas | 7-5 6-1 |
| 2008-02-25 | Acapulco | R32 | hard | Jill Craybas | 6-2 6-2 |
| 2003-09-15 | Shanghai | QF | hard | Rossana De Los Rios | 2-6 7-5 7-5 |
| 2000-05-01 | Virginia Beach 25K | SF | clay | Rossana De Los Rios | 6-2 4-6 6-3 |
Averages over each player's completed matches in the selected window (71 vs 12). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About