| Saturday, 17/04/1999 | Devonport City - George Town | 4:0 | ||||||
| Saturday, 24/04/1999 | Burnie United - Devonport City | 1:3 | ||||||
| Saturday, 01/05/1999 | Northern Rangers - Devonport City | 2:7 | ||||||
| Saturday, 08/05/1999 | Riverside Olympic - Devonport City | 1:3 | ||||||
| Saturday, 15/05/1999 | North Launceston Eagles - Devonport City | 2:2 | ||||||
| Saturday, 22/05/1999 | Devonport City - Launceston City | 3:0 | ||||||
| Saturday, 29/05/1999 | Devonport City - Western Knights | 4:1 | ||||||
| Sunday, 06/06/1999 | Ulverstone - Devonport City | 2:3 | ||||||
| Friday, 11/06/1999 | Devonport City - Somerset | 6:1 | ||||||
| Saturday, 19/06/1999 | Devonport City - Launceston | 1:0 | ||||||
| Saturday, 03/07/1999 | George Town - Devonport City | 0:0 | ||||||
| Friday, 09/07/1999 | Devonport City - Burnie United | 3:0 | ||||||
| Saturday, 17/07/1999 | Devonport City - Northern Rangers | 9:0 | ||||||
| Saturday, 24/07/1999 | Launceston - Devonport City | 2:2 | ||||||
| Saturday, 31/07/1999 | Devonport City - North Launceston Eagles | 8:1 | ||||||
| Saturday, 07/08/1999 | Launceston City - Devonport City | 0:9 | ||||||
| Saturday, 14/08/1999 | Western Knights - Devonport City | 1:4 | ||||||
| Friday, 20/08/1999 | Devonport City - Ulverstone | 1:1 | ||||||
| Sunday, 29/08/1999 | Somerset - Devonport City | 1:4 | ||||||
| Saturday, 04/09/1999 | Devonport City - Riverside Olympic | 2:3 |