Pietro Angelini defeated Riccardo Ciruolo 6-2 6-2 in the Italy 2 Masters 4 round of 32 on clay. The upset overturned the form book — Riccardo Ciruolo came in leading the head-to-head 2–0. Pietro Angelini claimed a first win over Riccardo Ciruolo in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 3 | R16 | clay | Riccardo Ciruolo | 7-5 3-6 7-5 |
| 1996-04-06 | Italy 1 Masters 1 | R32 | clay | Riccardo Ciruolo | 7-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.