Jason Cook defeated Jason Weir Smith 6-3 6-7 6-3 in the USA F16 round of 64 on hard. The upset overturned the form book — Jason Weir Smith came in leading the head-to-head 1–0. Jason Cook claimed a first win over Jason Weir Smith in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-16 | USA 4 Masters 4 | QF | hard | Jason Weir Smith | 6-3 6-2 |