Marco Monnecchi defeated Matteo Colla 5-7 6-1 7-5 in the Italy 3 Masters 3 round of 32 on clay. The upset overturned the form book — Matteo Colla came in leading the head-to-head 2–0, but Marco Monnecchi had been the form player, winning 4 of their last 9 on clay. Marco Monnecchi claimed a first win over Matteo Colla in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 2 | R32 | clay | Matteo Colla | 6-7 6-1 6-1 |
| 1997-06-28 | Italy 4 Masters 3 | R32 | clay | Matteo Colla | 6-1 6-0 |