Jeff Williams defeated Doug Root 7-5 6-3 in the USA F23 round of 16 on hard. The upset overturned the form book — Doug Root came in leading the head-to-head 1–0, but Jeff Williams had been the form player, winning 4 of their last 9 on hard. Jeff Williams claimed a first win over Doug Root in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-09 | USA F14 | R64 | hard | Doug Root | 6-7 7-6 5-1 |