| Saturday, 25/03/2000 | South Caulfield - Brandon Park | 2:1 | ||||||
| Saturday, 01/04/2000 | South Caulfield - Dandenong City | 2:2 | ||||||
| Saturday, 08/04/2000 | Dandenong Inter - South Caulfield | 2:0 | ||||||
| Sunday, 16/04/2000 | South Caulfield - North Caulfield | 1:5 | ||||||
| Saturday, 29/04/2000 | Dingley City - South Caulfield | 2:2 | ||||||
| Saturday, 06/05/2000 | South Caulfield - Newborough/Yallourn United | 1:0 | ||||||
| Saturday, 13/05/2000 | Noble Park United - South Caulfield | 3:1 | ||||||
| Saturday, 20/05/2000 | South Caulfield - Waverley Wanderers | 1:5 | ||||||
| Saturday, 27/05/2000 | South Caulfield - Heatherton United | 3:5 | ||||||
| Saturday, 03/06/2000 | Ashburton - South Caulfield | 4:1 | ||||||
| Saturday, 10/06/2000 | South Caulfield - Braeside United | 0:2 | ||||||
| Saturday, 17/06/2000 | Brandon Park - South Caulfield | 3:0 | ||||||
| Saturday, 24/06/2000 | Dandenong City - South Caulfield | 4:0 | ||||||
| Saturday, 01/07/2000 | South Caulfield - Dandenong Inter | 1:0 | ||||||
| Sunday, 09/07/2000 | North Caulfield - South Caulfield | 2:2 | ||||||
| Saturday, 15/07/2000 | South Caulfield - Dingley City | 1:1 | ||||||
| Saturday, 22/07/2000 | Newborough/Yallourn United - South Caulfield | 2:0 | ||||||
| Saturday, 05/08/2000 | South Caulfield - Noble Park United | 1:4 | ||||||
| Saturday, 12/08/2000 | Waverley Wanderers - South Caulfield | 4:1 | ||||||
| Saturday, 19/08/2000 | Heatherton United - South Caulfield | 3:1 | ||||||
| Saturday, 26/08/2000 | South Caulfield - Ashburton | 1:4 | ||||||
| Saturday, 09/09/2000 | Braeside United - South Caulfield | 2:0 |