Doug Root defeated Jason Cook 3-6 7-6 6-1 in the USA F13 round of 64 on hard. Doug Root extended 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 |
| 1999-06-14 | USA F7 | R64 | hard | Jason Cook | 7-6 6-7 7-6 |