Doug Flach defeated Dick Bosse 3-6 6-4 6-4 in the USA 2 Masters 2 round of 64 on clay. The upset overturned the form book — Dick Bosse came in leading the head-to-head 1–0. Doug Flach claimed a first win over Dick Bosse in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1992-06-01 | USA 3 Masters 4 | SF | hard | Dick Bosse | 4-6 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.