Jason Cook defeated Christian Hill 7-6 6-2 in the USA 2 Masters 4 round of 64 on hard. The upset overturned the form book — Christian Hill came in leading the head-to-head 1–0. Jason Cook claimed a first win over Christian Hill in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 3 | R32 | hard | Christian Hill | 2-6 7-5 6-4 |