Jason Cook defeated Doug Root 7-6 6-7 7-6 in the USA F7 round of 64 on hard. The upset overturned the form book — Doug Root came in leading the head-to-head 2–0. Jason Cook claimed a first win over Doug Root in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-09 | USA F14 | R16 | hard | Doug Root | 4-6 7-6 6-3 |
| 1999-08-02 | USA F13 | R64 | hard | Doug Root | 3-6 7-6 6-1 |