Stefano Cobolli defeated Matteo Colla 2-6 6-4 6-1 in the Italy 2 4 round of 32 on clay. Stefano Cobolli extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-05-26 | Italy 2 1 | F | clay | Matteo Colla | 7-6(4) 6-2 |
| 2003-05-26 | Italy 2 3 | R16 | clay | Matteo Colla | 6-3 6-0 |
| 2000-06-19 | Italy 3 4 | SF | clay | Matteo Colla | 6-3 6-0 |
| 1997-08-02 | Italy 5 Masters 1 | QF | clay | Stefano Cobolli | 4-6 6-4 6-4 |
| 1996-06-29 | Italy 3 Masters 2 | R16 | clay | Stefano Cobolli | 7-6 6-1 |
| 1995-07-29 | Italy 4 Masters 3 | R16 | clay | Stefano Cobolli | 7-6 7-5 |