Kepler Orellana defeated Luke Smith 3-6 7-6 6-4 in the Jamaica F2 round of 16 on hard. The result followed the form book — Kepler Orellana came in leading the head-to-head 1–0. Kepler Orellana extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-05-13 | Jamaica F5 | F | hard | Kepler Orellana | 7-5 4-6 7-5 |