Riccardo Ciruolo defeated Matteo Colla 7-5 6-4 in the Italy 1 Masters 4 qualifying round on clay. The upset overturned the form book — Matteo Colla came in leading the head-to-head 1–0, but Riccardo Ciruolo had been the form player, winning 2 of their last 4 on clay. Riccardo Ciruolo claimed a first win over Matteo Colla in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-12 | Italy F6 | QF | clay | Matteo Colla | 6-1 |