Alaaddin Karagoz defeated Alessandro Tombolini 6-4 4-6 6-3 in the Turkey 2 Masters 2 round of 32 on hard. The upset overturned the form book — Alessandro Tombolini came in leading the head-to-head 1–0. Alaaddin Karagoz claimed a first win over Alessandro Tombolini in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-06-01 | Turkey 1 Masters 2 | R32 | hard | Alessandro Tombolini | 6-2 6-3 |