Lee Pearson defeated Jordan Kerr 7-6 3-6 7-6 in the Australia F4 round of 32 on grass. The upset overturned the form book — Jordan Kerr came in leading the head-to-head 3–1. Lee Pearson narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-03-24 | Australia 2 4 | R32 | hard | Lee Pearson | 4-6 6-4 6-3 |
| 2000-02-21 | Australia 1 Masters 4 | QF | hard | Jordan Kerr | 6-4 6-4 |
| 1999-11-22 | Australia F4 | R32 | grass | Jordan Kerr | 6-4 6-3 |
| 1998-11-25 | Australia F4 | R32 | grass | Jordan Kerr | 6-3 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.