Jaymon Crabb defeated Andrew Painter 6-4 7-5 in the Adelaide qualifying round of 32 on hard. The upset overturned the form book — Andrew Painter came in leading the head-to-head 1–0, but Jaymon Crabb had been the form player, winning 4 of their last 5 on hard. Jaymon Crabb claimed a first win over Andrew Painter in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-04-07 | New Zealand Masters 4 | R16 | hard | Andrew Painter | 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.