Filippo Messori defeated Riccardo Ciruolo 6-4 6-7 6-1 in the Italy 4 1 qualifying round on clay. The result followed the form book — Filippo Messori came in leading the head-to-head 3–0. Filippo Messori extended the head-to-head to 4–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-26 | Italy F14 | QF | clay | Filippo Messori | 4-6 7-6 6-3 |
| 1995-07-01 | Italy 3 Masters 1 | R16 | clay | Filippo Messori | 6-2 6-3 |
| 1995-07-01 | Italy 3 Masters 4 | QF | clay | Filippo Messori | 4-6 6-2 6-4 |