Stefania Chieppa defeated Federica Di Sarra 6-3 6-7 6-0 in the Rome-Tevere Remo 25K round of 32 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 |
| 2007-10-15 | Settimo San Pietro 10K | QF | clay | Stefania Chieppa | 6-4 7-5 |
| 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.