Damien Roberts defeated Nikos Rovas 6-2 6-3 in the Greece F2 qualifying round on hard. The upset overturned the form book — Nikos Rovas came in leading the head-to-head 1–0. Damien Roberts claimed a first win over Nikos Rovas in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | Greece F1 | SF | hard | Nikos Rovas | 6-3 2-6 6-1 |