Matthew Breen defeated Tom Chicoine 4-6 6-4 6-2 in the USA F11 round of 64 on hard. The upset overturned the form book — Tom Chicoine came in leading the head-to-head 1–0. Matthew Breen claimed a first win over Tom Chicoine in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-10 | USA 2 Masters 1 | R16 | hard | Tom Chicoine | 6-4 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.