| Sunday, 18/04/1999 | Hobart Wanderers - Christian United | 2:1 | ||||||
| Sunday, 25/04/1999 | Derwent United - Hobart Wanderers | 0:7 | ||||||
| Sunday, 02/05/1999 | DOSA - Hobart Wanderers | 1:1 | ||||||
| Sunday, 09/05/1999 | University Grads - Hobart Wanderers | 1:1 | ||||||
| Sunday, 16/05/1999 | Barnstoneworth - Hobart Wanderers | 2:2 | ||||||
| Sunday, 30/05/1999 | Hobart Wanderers - New Town Eagles | 2:0 | ||||||
| Sunday, 06/06/1999 | University Bohemians - Hobart Wanderers | 2:6 | ||||||
| Saturday, 19/06/1999 | Hobart Wanderers - University Dinamo | 2:0 | ||||||
| Sunday, 27/06/1999 | Christian United - Hobart Wanderers | 0:1 | ||||||
| Saturday, 03/07/1999 | Hobart Wanderers - Derwent United | 6:2 | ||||||
| Saturday, 10/07/1999 | Hobart Wanderers - DOSA | 9:0 | ||||||
| Saturday, 17/07/1999 | Hobart Wanderers - University Grads | 5:1 | ||||||
| Sunday, 25/07/1999 | Hobart Wanderers - Barnstoneworth | 1:0 | ||||||
| Saturday, 31/07/1999 | New Norfolk - Hobart Wanderers | 1:2 | ||||||
| Sunday, 08/08/1999 | New Town Eagles - Hobart Wanderers | 2:4 | ||||||
| Saturday, 14/08/1999 | Hobart Wanderers - University Bohemians | 12:1 | ||||||
| Sunday, 22/08/1999 | University Dinamo - Hobart Wanderers | 0:3 | ||||||
| Saturday, 28/08/1999 | Hobart Wanderers - New Norfolk | 5:2 |