Gabriel Montilla defeated Ryan Russell 7-6 3-6 6-1 in the Jamaica F10 qualifying round on hard. The upset overturned the form book — Ryan Russell came in leading the head-to-head 1–0. Gabriel Montilla claimed a first win over Ryan Russell in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-04-09 | Davis Cup G2 PO: PUR vs JAM | RR | hard | Ryan Russell | 6-7 6-3 6-0 6-2 |