| Saturday, 20/03/1999 | Reddish Reserve | North Coburg United - South Wantirna | 3:1 | |||||
| Monday, 05/04/1999 | JT Gray Reserve | Williamstown - North Coburg United | 2:2 | |||||
| Saturday, 10/04/1999 | Reddish Reserve | North Coburg United - South Springvale | 0:0 | |||||
| Saturday, 17/04/1999 | Campbell Reserve | Moreland City - North Coburg United | 2:1 | |||||
| Saturday, 24/04/1999 | Reddish Reserve | North Coburg United - Stonnington City | 4:1 | |||||
| Saturday, 01/05/1999 | Laverton Park | Laverton Park - North Coburg United | 2:0 | |||||
| Saturday, 08/05/1999 | Reddish Reserve | North Coburg United - Banyule City | 1:1 | |||||
| Saturday, 15/05/1999 | Hosken Reserve | Pascoe Vale - North Coburg United | 0:4 | |||||
| Saturday, 22/05/1999 | Esther Park | Mooroolbark - North Coburg United | 0:1 | |||||
| Saturday, 29/05/1999 | Reddish Reserve | North Coburg United - Bell Park | 1:0 | |||||
| Saturday, 05/06/1999 | Laura Douglas Reserve | Broadmeadows City - North Coburg United | 2:4 | |||||
| Saturday, 12/06/1999 | Reddish Reserve | North Coburg United - Fitzroy City | 0:2 | |||||
| Monday, 14/06/1999 | Keilor Park Reserve | Keilor Park - North Coburg United | 1:2 | |||||
| Saturday, 19/06/1999 | Cretan Village | South Wantirna - North Coburg United | 0:1 | |||||
| Saturday, 26/06/1999 | Reddish Reserve | North Coburg United - Williamstown | 6:2 | |||||
| Saturday, 03/07/1999 | Warner Reserve | South Springvale - North Coburg United | 6:0 | |||||
| Saturday, 10/07/1999 | Reddish Reserve | North Coburg United - Moreland City | 3:1 | |||||
| Saturday, 17/07/1999 | Kooyong Park | Stonnington City - North Coburg United | 3:1 | |||||
| Saturday, 24/07/1999 | Reddish Reserve | North Coburg United - Laverton Park | 1:2 | |||||
| Saturday, 31/07/1999 | Yallambie Park | Banyule City - North Coburg United | 1:2 | |||||
| Saturday, 07/08/1999 | Reddish Reserve | North Coburg United - Pascoe Vale | 5:1 | |||||
| Saturday, 14/08/1999 | Reddish Reserve | North Coburg United - Mooroolbark | 1:0 | |||||
| Saturday, 28/08/1999 | Bell Park Sports Club | Bell Park - North Coburg United | 0:2 | |||||
| Saturday, 04/09/1999 | Reddish Reserve | North Coburg United - Broadmeadows City | 2:1 | |||||
| Saturday, 11/09/1999 | Fairfield Park | Fitzroy City - North Coburg United | 3:0 | |||||
| Saturday, 18/09/1999 | Reddish Reserve | North Coburg United - Keilor Park | 3:1 |