Donavan September advanced when Marq Foster retired 6-4 3-1 in the USA F8 round of 64. Donavan September extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-10 | USA F3 | R64 | clay | Marq Foster | 6-2 6-3 |
| 1998-03-27 | USA 1 Masters 1 | R64 | hard | Donavan September | 3-6 6-2 6-2 |
| 1996-04-05 | USA 1 Masters 2 | R32 | hard | Donavan September | 6-3 6-3 |