Jaymon Crabb defeated Chris Rae 4-6 7-5 6-2 in the Australia F3 round of 32 on grass. The upset overturned the form book — Chris Rae came in leading the head-to-head 1–0. Jaymon Crabb claimed a first win over Chris Rae in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Australia F2 | R16 | clay | Chris Rae | 6-3 3-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.