Elia Grossi advanced when Florian Allgauer retired 6-3 2-0 in the Italy 1 1 qualifying round. Elia Grossi extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-04-24 | Germany F1 | R32 | hard | Elia Grossi | 6-3 6-3 |
| 1999-05-03 | Italy F6 | QF | clay | Florian Allgauer | 6-1 6-4 |
| 1999-04-26 | Italy F5 | F | clay | Elia Grossi | 6-2 1-6 7-6 |
| 1997-06-28 | Italy 4 Masters 3 | QF | clay | Florian Allgauer | 6-1 6-1 |