Jason Cook defeated Brandon Kramer 6-4 6-0 in the USA F22B round of 16 on clay. The upset overturned the form book — Brandon Kramer came in leading the head-to-head 1–0. Jason Cook claimed a first win over Brandon Kramer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 2 | R64 | hard | Brandon Kramer | 4-6 6-4 6-3 |