Filippo Volandri defeated Andrea Grasselli 6-4 5-7 6-3 in the Italy 2 Masters 4 round of 32 on clay. Filippo Volandri extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 2 | R16 | clay | Filippo Volandri | 6-2 6-3 |
| 1998-08-01 | Italy 3 Masters 4 | QF | clay | Andrea Grasselli | 7-5 4-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.