Jordan Kerr defeated Leigh Holland 6-1 6-1 in the Australia 1 Masters 1 round of 32 on hard. The upset overturned the form book — Leigh Holland came in leading the head-to-head 4–0. Jordan Kerr claimed a first win over Leigh Holland in five meetings, narrowing 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 |
| 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 |
| 1998-04-07 | New Zealand Masters 2 | R32 | hard | Leigh Holland | 6-1 0-6 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.