Alessandro Tombolini defeated Giuseppe Montenet 6-3 6-1 in the Switzerland 3 Masters 2 round of 16 on carpet. The upset overturned the form book — Giuseppe Montenet came in leading the head-to-head 2–0. Alessandro Tombolini claimed a first win over Giuseppe Montenet in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-26 | Italy F14 | R32 | clay | Giuseppe Montenet | 2-6 7-5 6-4 |
| 1998-06-27 | Italy 2 Masters 1 | R16 | clay | Giuseppe Montenet | 7-5 3-6 6-2 |