Matteo Colla defeated Marco Monnecchi 6-1 6-0 in the Italy 4 Masters 3 round of 32 on clay. Matteo Colla extended 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 |
| 1996-06-29 | Italy 3 Masters 3 | R32 | clay | Marco Monnecchi | 5-7 6-1 7-5 |