Ryan Russell defeated Gabriel Montilla 6-7 6-3 6-0 6-2 in the PUR vs JAM round robin on hard. The upset overturned the form book — Gabriel Montilla came in leading the head-to-head 1–0, but Ryan Russell had been the form player, winning 3 of their last 8 on hard. Ryan Russell claimed a first win over Gabriel Montilla in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-07-15 | Jamaica F10 | QF | hard | Gabriel Montilla | 7-6(3) 3-6 6-1 |