Jason Weir Smith defeated Jason Cook 6-3 6-2 in the USA 4 Masters 4 qualifying round on hard. The upset overturned the form book — Jason Cook came in leading the head-to-head 1–0. Jason Weir Smith claimed a first win over Jason Cook in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-25 | USA F16 | R64 | hard | Jason Cook | 6-3 6-7 6-3 |