Matteo Colla defeated Gabrio Castrichella 7-5 6-3 in the Italy 4 Masters 3 round of 32 on clay. The upset overturned the form book — Gabrio Castrichella came in leading the head-to-head 1–0. Matteo Colla claimed a first win over Gabrio Castrichella in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-05-25 | Italy F7 | R16 | clay | Gabrio Castrichella | 7-6 6-1 |