Chris Pressley defeated Vince Mackey 6-4 6-1 in the USA 6 Masters 3 qualifying round on hard. The upset overturned the form book — Vince Mackey came in leading the head-to-head 1–0, but Chris Pressley had been the form player, winning 2 of their last 5 on hard. Chris Pressley claimed a first win over Vince Mackey in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-09-15 | USA 5 Masters 2 | R32 | hard | Vince Mackey | 6-4 4-6 6-3 |