| Monday, 01/02/1999 | Green Gully Reserve | Green Gully Cavaliers - Melbourne Raiders | 1:1 | |||||
| Sunday, 07/02/1999 | Epping Soccer Stadium | Melbourne Raiders - Fawkner Blues | 2:1 | |||||
| Sunday, 14/02/1999 | Kingston Heath Reserve | Bentleigh Greens - Melbourne Raiders | 1:1 | |||||
| Sunday, 21/02/1999 | Epping Soccer Stadium | Melbourne Raiders - Altona East Phoenix | 4:0 | |||||
| Sunday, 28/02/1999 | Goodyear Stadium | Preston Lions - Melbourne Raiders | 3:1 | |||||
| Saturday, 06/03/1999 | Epping Soccer Stadium | Melbourne Raiders - Port Melbourne Sharks | 0:2 | |||||
| Monday, 15/03/1999 | Veneto Club | Bulleen Inter Kings - Melbourne Raiders | 0:1 | |||||
| Monday, 22/03/1999 | Epping Soccer Stadium | Melbourne Raiders - Westvale | 1:0 | |||||
| Sunday, 28/03/1999 | Serbian Sports Centre | Springvale White Eagles - Melbourne Raiders | 3:0 | |||||
| Sunday, 11/04/1999 | Epping Soccer Stadium | Melbourne Raiders - Sunshine Georgies | 4:3 | |||||
| Saturday, 17/04/1999 | Paisley Park | Altona Magic - Melbourne Raiders | 2:2 | |||||
| Monday, 26/04/1999 | Epping Soccer Stadium | Melbourne Raiders - St Albans Saints | 1:0 | |||||
| Monday, 03/05/1999 | Epping Soccer Stadium | Melbourne Raiders - South Dandenong | 1:4 | |||||
| Monday, 10/05/1999 | Epping Soccer Stadium | Melbourne Raiders - Green Gully Cavaliers | 1:1 | |||||
| Sunday, 16/05/1999 | CB Smith Reserve | Fawkner Blues - Melbourne Raiders | 3:1 | |||||
| Monday, 24/05/1999 | Epping Soccer Stadium | Melbourne Raiders - Bentleigh Greens | 2:3 | |||||
| Sunday, 06/06/1999 | Paisley Park | Altona East Phoenix - Melbourne Raiders | 0:0 | |||||
| Monday, 14/06/1999 | Epping Soccer Stadium | Melbourne Raiders - Preston Lions | 0:2 | |||||
| Sunday, 20/06/1999 | SS Anderson Reserve | Port Melbourne Sharks - Melbourne Raiders | 5:0 | |||||
| Monday, 28/06/1999 | Epping Soccer Stadium | Melbourne Raiders - Bulleen Inter Kings | 0:2 | |||||
| Monday, 05/07/1999 | Green Gully Reserve | Westvale - Melbourne Raiders | 2:3 | |||||
| Monday, 12/07/1999 | Epping Soccer Stadium | Melbourne Raiders - Springvale White Eagles | 3:1 | |||||
| Sunday, 18/07/1999 | Chaplin Reserve | Sunshine Georgies - Melbourne Raiders | 2:4 | |||||
| Monday, 02/08/1999 | Epping Soccer Stadium | Melbourne Raiders - Altona Magic | 0:0 | |||||
| Sunday, 08/08/1999 | Churchill Reserve | St Albans Saints - Melbourne Raiders | 3:1 | |||||
| Sunday, 15/08/1999 | George Andrews Reserve | South Dandenong - Melbourne Raiders | 0:2 |