Kepler Orellana defeated Tres Davis 6-2 4-6 6-4 in the Jamaica F1 round of 16 on hard. Kepler Orellana extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-02-16 | USA F4 | R32 | hard | Kepler Orellana | 6-7(9) 6-2 6-2 |
| 2002-04-15 | Jamaica F2 | QF | hard | Tres Davis | 6-1 7-5 |