Leigh Holland defeated Jordan Kerr 6-1 0-6 6-0 in the New Zealand Masters 2 round of 32 on hard. The result followed the form book — Leigh Holland came in leading the head-to-head 3–1. Leigh Holland extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Ireland F1 | R16 | carpet | Leigh Holland | 7-6(5) 6-7(4) 6-4 |
| 2000-02-21 | Australia 1 Masters 1 | R32 | hard | Jordan Kerr | 6-1 6-1 |
| 1999-02-28 | Australia 1 Masters 4 | R32 | clay | Leigh Holland | 6-3 6-4 |
| 1998-05-10 | Australia 2 Masters 1 | R16 | hard | Leigh Holland | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.