| Friday, 19/03/1999 | Olympic Village | Heidelberg United - Western Suburbs | 2:0 | |||||
| Sunday, 28/03/1999 | Ralph Reserve | Western Suburbs - Springvale City | 1:1 | |||||
| Monday, 05/04/1999 | John Cain Memorial Park | Northcote City - Western Suburbs | 1:2 | |||||
| Sunday, 18/04/1999 | Ralph Reserve | Western Suburbs - Melbourne City | 4:0 | |||||
| Saturday, 24/04/1999 | HR Uren Reserve | Lalor United - Western Suburbs | 3:1 | |||||
| Sunday, 02/05/1999 | Ralph Reserve | Western Suburbs - North Geelong Warriors | 1:2 | |||||
| Friday, 07/05/1999 | Jack Edwards Reserve | Oakleigh - Western Suburbs | 1:2 | |||||
| Sunday, 16/05/1999 | Ralph Reserve | Western Suburbs - Richmond | 1:1 | |||||
| Saturday, 22/05/1999 | SS Anderson Reserve | Yarraville Glory - Western Suburbs | 1:0 | |||||
| Sunday, 30/05/1999 | Ralph Reserve | Western Suburbs - Werribee City | 2:0 | |||||
| Sunday, 06/06/1999 | Polish Sports & Recreation Centre | Westgate - Western Suburbs | 3:2 | |||||
| Saturday, 12/06/1999 | Ralph Reserve | Western Suburbs - Doncaster Rovers | 2:0 | |||||
| Monday, 14/06/1999 | Ralph Reserve | Western Suburbs - Kingston City | 3:2 | |||||
| Sunday, 20/06/1999 | Ralph Reserve | Western Suburbs - Heidelberg United | 1:1 | |||||
| Sunday, 27/06/1999 | Ross Reserve | Springvale City - Western Suburbs | 2:0 | |||||
| Sunday, 04/07/1999 | Ralph Reserve | Western Suburbs - Northcote City | 4:2 | |||||
| Sunday, 11/07/1999 | Polish Sports & Recreation Centre | Melbourne City - Western Suburbs | 2:3 | |||||
| Sunday, 18/07/1999 | Ralph Reserve | Western Suburbs - Lalor United | 0:0 | |||||
| Sunday, 25/07/1999 | Elcho Park | North Geelong Warriors - Western Suburbs | 3:2 | |||||
| Sunday, 01/08/1999 | Ralph Reserve | Western Suburbs - Oakleigh | 1:2 | |||||
| Sunday, 08/08/1999 | Kevin Bartlett Reserve | Richmond - Western Suburbs | 4:1 | |||||
| Sunday, 15/08/1999 | Ralph Reserve | Western Suburbs - Yarraville Glory | 3:1 | |||||
| Sunday, 29/08/1999 | Galvin Park Reserve | Werribee City - Western Suburbs | 4:4 | |||||
| Sunday, 05/09/1999 | Ralph Reserve | Western Suburbs - Westgate | 1:0 | |||||
| Sunday, 12/09/1999 | Anderson Park | Doncaster Rovers - Western Suburbs | 5:1 | |||||
| Sunday, 19/09/1999 | The Grange Reserve | Kingston City - Western Suburbs | 1:3 |