Simon Aspelin defeated Wynn Criswell 6-4 4-6 6-1 in the USA 5 Masters 4 qualifying round on hard. The upset overturned the form book — Wynn Criswell came in leading the head-to-head 1–0. Simon Aspelin claimed a first win over Wynn Criswell in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-09-05 | USA 5 Masters 2 | SF | hard | Wynn Criswell | 7-6 6-1 |