Chris Pressley defeated Chris Groer 6-3 6-2 in the USA 6 Masters 1 round of 64 on hard. The upset overturned the form book — Chris Groer came in leading the head-to-head 1–0, but Chris Pressley had been the form player, winning 4 of their last 8 on hard. Chris Pressley claimed a first win over Chris Groer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-06 | USA 5 Masters 3 | R16 | hard | Chris Groer | 4-6 6-3 7-5 |