Darko Madjarovski defeated Dustin Brown 6-2 7-6 in the Jamaica F16 round of 32 on hard. The result followed the form book — Darko Madjarovski came in leading the head-to-head 1–0. Darko Madjarovski extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-01-27 | Jamaica F2 | R32 | hard | Darko Madjarovski | 6-1 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.