Justin Layne defeated Yohny Romero 7-5 6-3 in the Bahamas F1 round of 32 on hard. The upset overturned the form book — Yohny Romero came in leading the head-to-head 1–0. Justin Layne claimed a first win over Yohny Romero in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | USA F16 | R32 | hard | Yohny Romero | 6-2 6-4 |