Dmitri Sitak defeated Darko Madjarovski 6-4 6-2 in the Jamaica F1 round of 16 on hard. The upset overturned the form book — Darko Madjarovski came in leading the head-to-head 1–0. Dmitri Sitak claimed a first win over Darko Madjarovski in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-01-12 | United Arab Emirates F1 | R32 | hard | Darko Madjarovski | 6-4 6-0 |