Tom Chicoine defeated Ryan Wolters 6-3 6-2 in the USA F8 round of 32 on hard. Tom Chicoine extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 2 | R16 | hard | Ryan Wolters | 6-3 6-2 |
| 1999-09-10 | USA 2 Masters 4 | R64 | hard | Tom Chicoine | 6-4 6-0 |