David Drew defeated Rich Benson 6-1 6-4 in the USA 5 Masters 2 qualifying round on hard. The upset overturned the form book — Rich Benson came in leading the head-to-head 1–0. David Drew claimed a first win over Rich Benson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1992-04-27 | USA 2 Masters 4 | R64 | clay | Rich Benson | 6-2 6-1 |