Greg Winchester defeated Tad Berkowitz 6-3 7-6 in the USA 3 Masters 4 round of 64 on hard. The upset overturned the form book — Tad Berkowitz came in leading the head-to-head 1–0. Greg Winchester claimed a first win over Tad Berkowitz in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-09-15 | USA 5 Masters 4 | R64 | hard | Tad Berkowitz | 6-4 6-7 6-3 |