Toby Mitchell defeated Andrew Painter 6-3 6-4 in the New Zealand Masters 2 round of 16 on hard. The result followed the form book — Toby Mitchell came in leading the head-to-head 2–1. Toby Mitchell extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-28 | Australia F1 | R16 | clay | Toby Mitchell | 6-1 6-2 |
| 1997-07-27 | Great Britain 3 Masters 3 | R16 | grass | Andrew Painter | 4-6 6-4 7-5 |
| 1997-05-10 | Australia 2 Masters 2 | QF | hard | Toby Mitchell | 5-7 7-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.