Stefano Cobolli defeated Matteo Colla 4-6 6-4 6-4 in the Italy 5 Masters 1 qualifying round 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 |
| 2003-05-26 | Italy 2 4 | R32 | clay | Stefano Cobolli | 2-6 6-4 6-1 |
| 2000-06-19 | Italy 3 4 | SF | clay | Matteo Colla | 6-3 6-0 |
| 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 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.