Giuseppe Montenet defeated Alessandro Tombolini 2-6 7-5 6-4 in the Italy F14 round of 32 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 |
| 1998-06-27 | Italy 2 Masters 1 | R16 | clay | Giuseppe Montenet | 7-5 3-6 6-2 |