Rob Chess defeated Wynn Criswell 6-4 4-6 6-1 in the USA 4 Masters 4 round of 64 on hard. The result followed the form book — Rob Chess came in leading the head-to-head 1–0. Rob Chess extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-07-19 | USA 4 Masters 3 | R32 | hard | Rob Chess | 6-2 6-3 |