Massimo Calvelli defeated Gabrio Castrichella 2-6 6-4 6-4 in the Italy 2 Masters 3 qualifying round on clay. Massimo Calvelli extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-04-06 | Italy 1 Masters 2 | R16 | clay | Gabrio Castrichella | 6-1 7-6 |
| 1995-04-01 | Italy 1 Masters 1 | R16 | clay | Massimo Calvelli | 3-6 7-6 6-4 |