Ryan Wolters defeated Tom Chicoine 6-3 6-2 in the USA 2 Masters 2 round of 16 on hard. The upset overturned the form book — Tom Chicoine came in leading the head-to-head 2–0. Ryan Wolters claimed a first win over Tom Chicoine in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 4 | R64 | hard | Tom Chicoine | 6-4 6-0 |
| 1999-06-21 | USA F8 | R32 | hard | Tom Chicoine | 6-3 6-2 |