Jelena Jankovic defeated Jill Craybas 6-4 3-6 6-3 in the Charleston round of 64 on clay. The upset overturned the form book — Jill Craybas came in defending last year's round of 16. Jelena Jankovic extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-02-27 | Kuala Lumpur | R16 | hard | Jelena Jankovic | 6-2 6-0 |
| 2006-04-03 | Amelia Island | R64 | clay | Jill Craybas | 2-6 7-6(8) 4-0 RET |
| 2006-01-16 | Australian Open | R128 | hard | Jelena Jankovic | 6-2 4-6 6-4 |
| 2004-01-19 | Australian Open | R64 | hard | Jill Craybas | 6-4 2-6 8-6 |
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 (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About