Carolina Pillot defeated Anna Giulia Remondina 6-1 6-1 in the Monteroni D'Arbia 25K round of 32 on clay. The upset overturned the form book — Anna Giulia Remondina came in leading the head-to-head 4–0, but Carolina Pillot had been the form player, winning 4 of their last 8 on clay. Carolina Pillot claimed a first win over Anna Giulia Remondina in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2014-09-29 | Santa Margherita Di Pula 10K | R32 | clay | Anna Giulia Remondina | 6-3 4-6 6-3 |
| 2009-10-12 | Settimo San Pietro 10K | R32 | clay | Anna Giulia Remondina | 6-3 6-2 |
| 2009-07-27 | Gardone Val Trompia 10K | R32 | clay | Anna Giulia Remondina | 5-7 6-2 6-1 |
| 2008-10-13 | Settimo San Pietro 10K | R16 | clay | Anna Giulia Remondina | 7-6(5) 3-6 7-6(0) |