Carlo Santoro defeated Elia Grossi 6-3 6-4 in the Italy 3 Masters 3 qualifying round on clay. Carlo Santoro extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-24 | Italy F8 | QF | clay | Elia Grossi | 4-2 4-2 4-1 |
| 1999-02-13 | Italy 1 Masters 4 | R16 | clay | Carlo Santoro | 0-6 6-2 6-2 |
| 1997-06-28 | Italy 4 Masters 4 | R16 | clay | Elia Grossi | 7-5 6-2 |
| 1996-04-06 | Italy 1 Masters 2 | R16 | clay | Carlo Santoro | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.