Christian Hill defeated Jason Cook 2-6 7-5 6-4 in the USA 2 Masters 3 round of 32 on hard. The upset overturned the form book — Jason Cook came in leading the head-to-head 1–0. Christian Hill claimed a first win over Jason Cook in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 4 | R64 | hard | Jason Cook | 7-6 6-2 |