Jonathan Leach defeated Kip Brady 6-3 6-3 in the USA 3 Masters 4 qualifying round on hard. The upset overturned the form book — Kip Brady came in leading the head-to-head 1–0, but Jonathan Leach had been the form player, winning 4 of their last 6 on hard. Jonathan Leach claimed a first win over Kip Brady in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-09-15 | USA 5 Masters 2 | R32 | hard | Kip Brady | 2-6 6-4 6-3 |