Simon Aspelin defeated Jason Cook 6-2 6-0 in the USA 5 Masters 2 qualifying round on hard. The upset overturned the form book — Jason Cook came in leading the head-to-head 1–0. Simon Aspelin claimed a first win over Jason Cook in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-16 | USA 4 Masters 4 | R64 | hard | Jason Cook | 6-4 7-6 |