Wynn Criswell defeated Tad Berkowitz 6-2 6-3 in the Canada F2 round of 32 on hard. The upset overturned the form book — Tad Berkowitz came in leading the head-to-head 1–0. Wynn Criswell claimed a first win over Tad Berkowitz in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-07-19 | USA 4 Masters 2 | R64 | hard | Tad Berkowitz | 7-6 6-2 |