Graham Gilles defeated Wynn Criswell 6-3 6-7 6-3 in the USA 2 Masters 2 round of 64 on clay. The upset overturned the form book — Wynn Criswell came in leading the head-to-head 2–0. Graham Gilles claimed a first win over Wynn Criswell in three meetings, narrowing 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 |
| 1995-10-13 | USA 6 Masters 3 | R64 | hard | Wynn Criswell | 6-7 7-6 6-4 |