Filippo Messori defeated Massimo Ocera 6-2 7-6 in the Italy 4 2 qualifying round on clay. The result followed the form book — Filippo Messori came in leading the head-to-head 1–0. Filippo Messori extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Italy 4 3 | R16 | clay | Filippo Messori | 6-4 6-0 |