Matteo Colla defeated Mattia Livraghi 2-6 6-3 6-3 in the Milan qualifying round of 32 on carpet. The result followed the form book — Matteo Colla came in leading the head-to-head 1–0. Matteo Colla extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Italy F4 | R16 | clay | Matteo Colla | 6-2 6-1 |