Andrew Painter defeated Jaymon Crabb 6-3 7-6 in the New Zealand Masters 4 round of 16 on hard. The upset overturned the form book — Jaymon Crabb came in leading the head-to-head 1–0. Andrew Painter claimed a first win over Jaymon Crabb in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-01-03 | Adelaide | Q32 | hard | Jaymon Crabb | 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.