Annalisa Bona defeated Stefania Chieppa 6-2 6-2 in the Castel Gandolfo 10K round of 32 on clay. The upset overturned the form book — Stefania Chieppa came in leading the head-to-head 3–0. Annalisa Bona claimed a first win over Stefania Chieppa in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-05-08 | Casale 10K | SF | clay | Stefania Chieppa | 6-1 7-5 |
| 2005-05-09 | Casale 10K | R16 | clay | Stefania Chieppa | 6-4 6-3 |
| 2004-11-01 | RomeCanottieri 10K | R32 | clay | Stefania Chieppa | 5-7 6-1 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.