| Saturday, 05/04/1969 | East Melbourne Helvetic - St. Kilda | 8:2 | ||||||
| Saturday, 12/04/1969 | St. Kilda - Brighton | 2:3 | ||||||
| Saturday, 19/04/1969 | St. Kilda - Princes Park Hercules | 1:1 | ||||||
| Saturday, 26/04/1969 | Chelsea - St. Kilda | 0:2 | ||||||
| Saturday, 03/05/1969 | St. Kilda - Croydon City | 4:1 | ||||||
| Saturday, 10/05/1969 | Bayswater United - St. Kilda | 2:4 | ||||||
| Saturday, 17/05/1969 | St. Kilda - Glenroy United | 5:2 | ||||||
| Saturday, 24/05/1969 | University of Melbourne Blues - St. Kilda | 0:8 | ||||||
| Saturday, 31/05/1969 | St. Kilda - Heidelberg | 3:1 | ||||||
| Saturday, 07/06/1969 | Clayton - St. Kilda | 1:3 | ||||||
| Saturday, 14/06/1969 | St. Kilda - Ballarat | 3:3 | ||||||
| Saturday, 21/06/1969 | St. Kilda - East Melbourne Helvetic | 2:0 | ||||||
| Saturday, 28/06/1969 | Brighton - St. Kilda | 1:1 | ||||||
| Saturday, 05/07/1969 | Princes Park Hercules - St. Kilda | 1:1 | ||||||
| Saturday, 12/07/1969 | St. Kilda - Chelsea | 5:0 | ||||||
| Saturday, 19/07/1969 | Croydon City - St. Kilda | 5:2 | ||||||
| Saturday, 26/07/1969 | St. Kilda - Bayswater United | 4:0 | ||||||
| Saturday, 02/08/1969 | Glenroy United - St. Kilda | 1:2 | ||||||
| Saturday, 09/08/1969 | St. Kilda - University of Melbourne Blues | 3:1 | ||||||
| Saturday, 16/08/1969 | Heidelberg - St. Kilda | 1:6 | ||||||
| Saturday, 23/08/1969 | St. Kilda - Clayton | 1:2 | ||||||
| Saturday, 30/08/1969 | Ballarat - St. Kilda | 1:4 |