Colin Bennett defeated Charlie Singer 6-3 3-6 6-2 in the USA 4 Masters 2 round of 64 on hard. The upset overturned the form book — Charlie Singer came in leading the head-to-head 1–0. Colin Bennett claimed a first win over Charlie Singer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-09-09 | Great Britain 4 Masters 4 | R32 | hard | Charlie Singer | 6-0 6-4 |