Tom Chicoine defeated Zack Fleishman 4-6 6-1 6-4 in the USA F10 semi-final on hard. The result followed the form book — Tom Chicoine came in leading the head-to-head 2–0. Tom Chicoine extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 4 | QF | hard | Tom Chicoine | 7-6 6-4 |
| 1999-08-02 | USA F13 | SF | hard | Tom Chicoine | 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.