Stefano Cobolli defeated Milen Velev 6-2 2-6 6-1 in the Italy 8 1 round of 16 on hard. The upset overturned the form book — Milen Velev came in leading the head-to-head 2–0. Stefano Cobolli claimed a first win over Milen Velev in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-08 | Bulgaria 2 Masters 1 | R16 | hard | Milen Velev | 4-6 6-1 6-3 |
| 1996-09-08 | Bulgaria 2 Masters 2 | R16 | hard | Milen Velev | 4-6 6-4 6-2 |