Elia Grossi advanced when Fabio Beraldo retired 3-0 in the Italy 4 Masters 2 qualifying round. Elia Grossi extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-05-31 | Italy 3 Masters 2 | QF | clay | Elia Grossi | 7-6 2-6 6-2 |
| 1996-09-28 | Italy 5 Masters 1 | R16 | clay | Fabio Beraldo | 6-1 6-0 |
| 1996-06-29 | Italy 3 Masters 4 | R16 | clay | Fabio Beraldo | 3-6 7-6 6-1 |
| 1996-06-01 | Italy 2 Masters 2 | R16 | clay | Elia Grossi | 7-6 6-2 |
| 1996-04-06 | Italy 1 Masters 3 | QF | clay | Elia Grossi | 7-5 7-6 |
| 1994-07-30 | Italy 3 Masters 1 | R32 | clay | Fabio Beraldo | 6-2 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.