Giuseppe Montenet defeated Alessandro Tombolini 7-5 3-6 6-2 in the Italy 2 Masters 1 round of 16 on clay. Giuseppe Montenet extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-16 | Switzerland 3 Masters 2 | R16 | carpet | Alessandro Tombolini | 6-3 6-1 |
| 1999-07-26 | Italy F14 | R32 | clay | Giuseppe Montenet | 2-6 7-5 6-4 |