Jason Cook defeated Dustin Mauck 4-6 6-2 7-5 in the USA F15 round of 64 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 |
|---|---|---|---|---|---|
| 1999-06-14 | USA F7 | R16 | hard | Jason Cook | 3-6 6-3 6-2 |