Ben Mathias defeated Jay Gooding 7-5 6-4 in the Australia F3 round of 32 on grass. The upset overturned the form book — Jay Gooding came in leading the head-to-head 2–0. Ben Mathias claimed a first win over Jay Gooding in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-01 | Australia F2 | R32 | clay | Jay Gooding | 7-6 6-7 6-3 |
| 1999-09-19 | Australia 3 Masters 4 | R32 | hard | Jay Gooding | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.