Dmitri Sitak defeated Jose De Armas 7-5 6-4 in the Jamaica F1 round of 32 on hard. The upset overturned the form book — Jose De Armas came in leading the head-to-head 1–0. Dmitri Sitak claimed a first win over Jose De Armas in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-01-27 | Jamaica F2 | R16 | hard | Jose De Armas | 6-2 7-6(3) |