Nikos Rovas defeated Damien Roberts 6-3 2-6 6-1 in the Greece F1 semi-final on hard. The upset overturned the form book — Damien Roberts came in leading the head-to-head 1–0. Nikos Rovas claimed a first win over Damien Roberts in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-17 | Greece F2 | QF | hard | Damien Roberts | 6-2 6-3 |