Stefania Chieppa defeated Federica Di Sarra 6-4 7-5 in the Settimo San Pietro 10K qualifying round on clay. The upset overturned the form book — Federica Di Sarra came in leading the head-to-head 2–1. Stefania Chieppa narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-08-24 | Arezzo 10K | R32 | clay | Federica Di Sarra | 6-3 2-6 6-2 |
| 2009-07-13 | Rome-Tevere Remo 25K | R32 | clay | Stefania Chieppa | 6-3 6-7(3) 6-0 |
| 2007-05-14 | Caserta 10K | R32 | clay | Federica Di Sarra | 6-2 2-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.