Jay Gooding defeated Josh Tuckfield 7-6 7-6 in the Australia 3 Masters 2 qualifying round on hard. The upset overturned the form book — Josh Tuckfield came in leading the head-to-head 2–1, but Jay Gooding had been the form player, winning 6 of their last 8 on hard. Jay Gooding narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 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 |
| 1998-10-28 | Australia F1 | R32 | clay | Jay Gooding | 3-6 6-3 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.