Mitty Arnold defeated Keith Brill 7-5 6-1 in the USA F1 round of 32 on hard. Mitty Arnold extended 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 |
| 1999-01-11 | USA F2 | R64 | hard | Keith Brill | 6-4 7-6 |