Jose De Armas defeated Dmitri Sitak 6-2 7-6 in the Jamaica F2 round of 16 on hard. The upset overturned the form book — Dmitri Sitak came in leading the head-to-head 1–0. Jose De Armas claimed a first win over Dmitri Sitak in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-01-20 | Jamaica F1 | R32 | hard | Dmitri Sitak | 7-5 6-4 |