Diego Alvarez defeated Elia Grossi 6-3 6-1 in the Italy 3 Masters 2 round of 32 on clay. Diego Alvarez extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-31 | Italy F9 | QF | clay | Elia Grossi | 1-4 4-1 4-2 4-2 |
| 2000-06-19 | Italy 3 3 | F | clay | Diego Alvarez | 6-2 6-4 |
| 2000-03-11 | Italy 1 Masters 3 | SF | clay | Diego Alvarez | 6-1 6-1 |
| 2000-03-11 | Italy 1 Masters 4 | R16 | clay | Elia Grossi | 6-2 6-4 |