Huntley Montgomery defeated Ryan Newport 7-6 6-3 in the USA F5 round of 32 on hard. The result followed the form book — Huntley Montgomery came in leading the head-to-head 1–0. Huntley Montgomery extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-10-20 | USA F29 | R32 | hard | Huntley Montgomery | 6-3 6-2 |