Chris Rae defeated Jaymon Crabb 6-3 3-6 6-2 in the Australia F2 round of 16 on clay. The upset overturned the form book — Jaymon Crabb came in leading the head-to-head 1–0. Chris Rae claimed a first win over Jaymon Crabb in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Australia F3 | R32 | grass | Jaymon Crabb | 4-6 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.