Jaymon Crabb defeated Lee Pearson 7-5 6-3 in the Australia F3 round of 16 on grass. The upset overturned the form book — Lee Pearson came in leading the head-to-head 3–0. Jaymon Crabb claimed a first win over Lee Pearson in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-11-03 | Australia F3 | R16 | clay | Lee Pearson | 6-4 6-4 |
| 1998-11-18 | Australia F3 | R32 | grass | Lee Pearson | 4-6 6-3 6-4 |
| 1996-09-22 | Australia 2 Masters 2 | R32 | hard | Lee Pearson | 7-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.