| Saturday, 25/03/2000 | Glenroy - South Yarra | 6:1 | ||||||
| Saturday, 01/04/2000 | Keon Park - Glenroy | 3:2 | ||||||
| Saturday, 08/04/2000 | Glenroy - Ballarat Red Devils | 1:0 | ||||||
| Saturday, 15/04/2000 | Broadmeadows United - Glenroy | 4:2 | ||||||
| Saturday, 29/04/2000 | Glenroy - Darebin United | 4:2 | ||||||
| Saturday, 06/05/2000 | University of Melbourne Blues - Glenroy | 1:1 | ||||||
| Saturday, 13/05/2000 | Whittlesea United - Glenroy | 1:2 | ||||||
| Saturday, 20/05/2000 | Glenroy - Melbourne University Rangers | 1:4 | ||||||
| Saturday, 27/05/2000 | Mill Park - Glenroy | 0:3 | ||||||
| Saturday, 03/06/2000 | Glenroy - Moreland United | 1:2 | ||||||
| Saturday, 10/06/2000 | Somerton City - Glenroy | 3:2 | ||||||
| Saturday, 17/06/2000 | South Yarra - Glenroy | 0:3 | ||||||
| Saturday, 24/06/2000 | Glenroy - Keon Park | 6:0 | ||||||
| Saturday, 01/07/2000 | Ballarat Red Devils - Glenroy | 1:4 | ||||||
| Saturday, 08/07/2000 | Glenroy - Broadmeadows United | 1:2 | ||||||
| Saturday, 15/07/2000 | Darebin United - Glenroy | 2:1 | ||||||
| Saturday, 22/07/2000 | Glenroy - University of Melbourne Blues | 1:2 | ||||||
| Saturday, 05/08/2000 | Glenroy - Whittlesea United | 6:2 | ||||||
| Saturday, 12/08/2000 | Melbourne University Rangers - Glenroy | 0:4 | ||||||
| Saturday, 19/08/2000 | Glenroy - Mill Park | 3:2 | ||||||
| Saturday, 26/08/2000 | Moreland United - Glenroy | 3:5 | ||||||
| Saturday, 09/09/2000 | Glenroy - Somerton City | 6:2 |