Josh Tuckfield defeated Sebastian Swierk 6-7 6-3 6-2 in the Australia 4 Masters 1 round of 32 on hard. The upset overturned the form book — Sebastian Swierk came in leading the head-to-head 4–1. Josh Tuckfield narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-07-10 | Turkey F3 | F | hard | Josh Tuckfield | 7-6(3) 6-4 |
| 2000-02-21 | Australia 1 Masters 2 | R16 | hard | Sebastian Swierk | 4-6 6-2 7-5 |
| 1999-11-22 | Australia F4 | R16 | grass | Sebastian Swierk | 6-3 3-0 |
| 1999-08-09 | USA F14 | R16 | hard | Sebastian Swierk | 5-7 6-1 7-6 |
| 1998-03-01 | Australia 1 Masters 2 | R32 | hard | Sebastian Swierk | 6-2 6-4 |