Rich Benson defeated David Drew 6-2 6-1 in the USA 2 Masters 4 round of 64 on clay. The upset overturned the form book — David Drew came in leading the head-to-head 1–0. Rich Benson claimed a first win over David Drew in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1991-10-21 | USA 5 Masters 2 | QF | hard | David Drew | 6-1 6-4 |