David Nainkin defeated Bret Richardson 0-6 6-3 6-3 in the Australia 2 Masters 3 semi-final on hard. The upset overturned the form book — Bret Richardson came in leading the head-to-head 2–0. David Nainkin claimed a first win over Bret Richardson in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1992-10-12 | Australia 3 Masters 2 | R16 | hard | Bret Richardson | 6-4 6-7 6-2 |
| 1991-08-12 | Australia 2 Masters 3 | R16 | hard | Bret Richardson | 7-5 3-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.