Tres Davis defeated Kepler Orellana 6-1 7-5 in the Jamaica F2 qualifying round on hard. The upset overturned the form book — Kepler Orellana came in leading the head-to-head 2–0. Tres Davis claimed a first win over Kepler Orellana in three meetings, narrowing 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 |
| 2002-04-08 | Jamaica F1 | R16 | hard | Kepler Orellana | 6-2 4-6 6-4 |