Matteo Colla defeated Massimo Dellacqua 6-0 6-2 in the Italy F2 qualifying round on clay. The upset overturned the form book — Massimo Dellacqua came in leading the head-to-head 3–0. Matteo Colla claimed a first win over Massimo Dellacqua in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 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.