Janne Ojala defeated Stefano Cobolli 6-4 7-6 in the Italy F5 round of 16 on clay. The upset overturned the form book — Stefano Cobolli came in leading the head-to-head 1–0, but Janne Ojala had been the form player, winning 5 of their last 8 on clay. Janne Ojala claimed a first win over Stefano Cobolli in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-06 | Egypt 2 Masters 3 | R16 | clay | Stefano Cobolli | 6-2 5-7 6-3 |