Jeff Williams defeated Tom Chicoine 6-4 6-2 in the USA F8 round of 32 on hard. The result followed the form book — Jeff Williams came in leading the head-to-head 2–0. Jeff Williams extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-04-17 | USA F10 | R16 | hard | Jeff Williams | 6-4 6-0 |
| 1999-09-10 | USA 2 Masters 3 | R64 | hard | Jeff Williams | 6-1 6-2 |