| Sunday, 21/03/1999 | Dorset Recreational Reserve | Croydon City Arrows - Geelong | 0:2 | |||||
| Saturday, 27/03/1999 | Gardiners Reserve | Old Scotch Waverley - Croydon City Arrows | 2:0 | |||||
| Saturday, 10/04/1999 | McPherson Park | Satellite City Rovers - Croydon City Arrows | 1:0 | |||||
| Saturday, 17/04/1999 | Dorset Recreational Reserve | Croydon City Arrows - East Richmond | 3:2 | |||||
| Saturday, 24/04/1999 | Reggio Calabria Club | Essendon Royals - Croydon City Arrows | 0:0 | |||||
| Saturday, 01/05/1999 | Dorset Recreational Reserve | Croydon City Arrows - Frankston Pines | 2:3 | |||||
| Saturday, 08/05/1999 | Partridge Reserve | Thomastown/Regent Raiders - Croydon City Arrows | 2:2 | |||||
| Saturday, 15/05/1999 | Dorset Recreational Reserve | Croydon City Arrows - Knox City | 1:1 | |||||
| Saturday, 22/05/1999 | Jubilee Park | Ringwood City - Croydon City Arrows | 2:2 | |||||
| Saturday, 29/05/1999 | Dorset Recreational Reserve | Croydon City Arrows - Cranbourne Comets | 1:2 | |||||
| Saturday, 05/06/1999 | Wilinda Park | Diamond Valley United - Croydon City Arrows | 0:2 | |||||
| Saturday, 12/06/1999 | Dorset Recreational Reserve | Croydon City Arrows - Altona City | 1:1 | |||||
| Monday, 14/06/1999 | Centenary Park | Frankston Strikers - Croydon City Arrows | 5:1 | |||||
| Saturday, 19/06/1999 | Stead Park | Geelong - Croydon City Arrows | 2:1 | |||||
| Saturday, 26/06/1999 | Dorset Recreational Reserve | Croydon City Arrows - Old Scotch Waverley | 0:1 | |||||
| Saturday, 03/07/1999 | Dorset Recreational Reserve | Croydon City Arrows - Satellite City Rovers | 1:2 | |||||
| Saturday, 10/07/1999 | Kevin Bartlett Reserve | East Richmond - Croydon City Arrows | 2:0 | |||||
| Saturday, 17/07/1999 | Dorset Recreational Reserve | Croydon City Arrows - Essendon Royals | 1:2 | |||||
| Saturday, 24/07/1999 | Monterey Reserve | Frankston Pines - Croydon City Arrows | 4:0 | |||||
| Saturday, 31/07/1999 | Dorset Recreational Reserve | Croydon City Arrows - Thomastown/Regent Raiders | 4:1 | |||||
| Saturday, 07/08/1999 | Egan Lee Reserve | Knox City - Croydon City Arrows | 4:0 | |||||
| Saturday, 14/08/1999 | Dorset Recreational Reserve | Croydon City Arrows - Ringwood City | 2:2 | |||||
| Saturday, 28/08/1999 | Comets Stadium | Cranbourne Comets - Croydon City Arrows | 4:2 | |||||
| Saturday, 04/09/1999 | Dorset Recreational Reserve | Croydon City Arrows - Diamond Valley United | 1:1 | |||||
| Saturday, 11/09/1999 | Kim Reserve | Altona City - Croydon City Arrows | 2:3 | |||||
| Saturday, 18/09/1999 | Dorset Recreational Reserve | Croydon City Arrows - Frankston Strikers | 0:2 |