Giulia Gatto Monticone defeated Stefania Chieppa 2-6 6-4 6-0 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 3–1. Giulia Gatto Monticone narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-10-12 | Settimo San Pietro 10K | SF | clay | Stefania Chieppa | 6-4 6-4 |
| 2009-08-03 | Monteroni 25K | R32 | clay | Giulia Gatto Monticone | 6-3 6-4 |
| 2006-05-08 | Casale 10K | R16 | clay | Stefania Chieppa | 6-3 6-3 |
| 2005-07-25 | Sezze 10K | R16 | clay | Stefania Chieppa | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.