Jay Gooding defeated Josh Tuckfield 3-6 6-3 6-1 in the Australia F1 round of 32 on clay. The upset overturned the form book — Josh Tuckfield came in leading the head-to-head 2–1. Jay Gooding narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-02 | Australia 3 Masters 2 | QF | hard | Jay Gooding | 7-6(5) 7-6(5) |
| 2000-02-21 | Australia 1 Masters 1 | QF | hard | Josh Tuckfield | 3-6 6-2 6-3 |
| 1999-07-19 | USA F11 | QF | hard | Josh Tuckfield | 3-6 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.