Matteo Colla advanced past Massimo Dellacqua via walkover in the Italy 3 Masters 3 qualifying round. Matteo Colla narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-05-07 | Italy F2 | QF | clay | Matteo Colla | 6-0 6-2 |
| 2000-05-15 | Italy F2 | F | clay | Massimo Dellacqua | 6-2 6-2 |
| 1999-07-26 | Italy F14 | R32 | clay | Massimo Dellacqua | 6-4 3-6 6-2 |
| 1999-04-20 | Italy F4 | R32 | clay | Massimo Dellacqua | 6-4 3-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.