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