Tad Berkowitz defeated Greg Winchester 6-4 6-7 6-3 in the USA 5 Masters 4 round of 64 on hard. The upset overturned the form book — Greg Winchester came in leading the head-to-head 1–0. Tad Berkowitz claimed a first win over Greg Winchester in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-06-09 | USA 3 Masters 4 | R64 | hard | Greg Winchester | 6-3 7-6 |