Keith Brill defeated Mitty Arnold 6-4 7-6 in the USA F2 round of 64 on hard. The upset overturned the form book — Mitty Arnold came in leading the head-to-head 2–0. Keith Brill claimed a first win over Mitty Arnold in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-23 | Central America Masters 3 | R32 | clay | Mitty Arnold | 6-1 6-4 |
| 1999-01-04 | USA F1 | R32 | hard | Mitty Arnold | 7-5 6-1 |