Doug Root defeated Jason Cook 4-6 7-6 6-3 in the USA F14 round of 16 on hard. Doug Root extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | USA F13 | R64 | hard | Doug Root | 3-6 7-6 6-1 |
| 1999-06-14 | USA F7 | R64 | hard | Jason Cook | 7-6 6-7 7-6 |