Chris Groer defeated Chris Pressley 4-6 6-3 7-5 in the USA 5 Masters 3 round of 16 on hard. The upset overturned the form book — Chris Pressley came in leading the head-to-head 1–0. Chris Groer claimed a first win over Chris Pressley in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-11 | USA 6 Masters 1 | R64 | hard | Chris Pressley | 6-3 6-2 |