Jason Cook defeated Dustin Mauck 3-6 6-3 6-2 in the USA F7 round of 16 on hard. The result followed the form book — Jason Cook came in leading the head-to-head 1–0. Jason Cook extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | USA F15 | R64 | hard | Jason Cook | 4-6 6-2 7-5 |