| Saturday, 31/03/2001 | Nunawading City - Chelsea | 2:1 | ||||||
| Saturday, 07/04/2001 | Chelsea - Ringwood City | 3:2 | ||||||
| Saturday, 21/04/2001 | Banyule City - Chelsea | 0:0 | ||||||
| Saturday, 28/04/2001 | Chelsea - Sandringham City | 3:1 | ||||||
| Saturday, 05/05/2001 | Keysborough - Chelsea | 1:3 | ||||||
| Saturday, 12/05/2001 | Chelsea - Monbulk | 1:2 | ||||||
| Saturday, 19/05/2001 | Seaford United - Chelsea | 3:5 | ||||||
| Saturday, 26/05/2001 | Chelsea - Lyndale United | 0:1 | ||||||
| Saturday, 02/06/2001 | Clifton Hill United - Chelsea | 0:1 | ||||||
| Saturday, 09/06/2001 | Chelsea - South Wantima | 3:0 | ||||||
| Saturday, 16/06/2001 | Endeavour United - Chelsea | 3:2 | ||||||
| Saturday, 23/06/2001 | Chelsea - Nunawading City | 2:0 | ||||||
| Saturday, 30/06/2001 | Ringwood City - Chelsea | 2:1 | ||||||
| Saturday, 07/07/2001 | Chelsea - Banyule City | 1:1 | ||||||
| Saturday, 14/07/2001 | Sandringham City - Chelsea | 1:1 | ||||||
| Saturday, 21/07/2001 | Chelsea - Keysborough | 1:1 | ||||||
| Saturday, 28/07/2001 | Monbulk - Chelsea | 1:1 | ||||||
| Saturday, 04/08/2001 | Chelsea - Seaford United | 0:2 | ||||||
| Saturday, 11/08/2001 | Lyndale United - Chelsea | 2:1 | ||||||
| Saturday, 18/08/2001 | Chelsea - Clifton Hill United | 1:3 | ||||||
| Saturday, 01/09/2001 | South Wantima - Chelsea | 2:2 | ||||||
| Saturday, 08/09/2001 | Chelsea - Endeavour United | 4:0 |