Wynn Criswell defeated Graham Gilles 6-7 7-6 6-4 in the USA 6 Masters 3 round of 64 on hard. Wynn Criswell extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-10-10 | USA 6 Masters 1 | R64 | hard | Wynn Criswell | 6-4 6-2 |
| 1996-05-17 | USA 2 Masters 2 | R64 | clay | Graham Gilles | 6-3 6-7 6-3 |