| Regular Season | Sunday, 23/03/1986 | Morwell Falcons - Caulfield City | 0:3 | ||||||
| Regular Season | Saturday, 29/03/1986 | Caulfield City - Northcote City | 5:3 | ||||||
| Regular Season | Sunday, 06/04/1986 | Western Suburbs - Caulfield City | 2:0 | ||||||
| Regular Season | Saturday, 12/04/1986 | Caulfield City - Croydon City | 0:3 | ||||||
| Regular Season | Saturday, 19/04/1986 | Caulfield City - Ringwood City | 5:1 | ||||||
| Regular Season | Sunday, 27/04/1986 | Springvale City - Caulfield City | 1:1 | ||||||
| Regular Season | Saturday, 03/05/1986 | Caulfield City - St Albans | 1:4 | ||||||
| Regular Season | Sunday, 11/05/1986 | Thomastown - Caulfield City | 1:0 | ||||||
| Regular Season | Saturday, 17/05/1986 | Caulfield City - Frankston Pines | 0:3 | ||||||
| Regular Season | Sunday, 25/05/1986 | Box Hill - Caulfield City | 3:0 | ||||||
| Regular Season | Saturday, 31/05/1986 | Caulfield City - Melbourne | 2:1 | ||||||
| Regular Season | Sunday, 08/06/1986 | Fawkner - Caulfield City | 0:1 | ||||||
| Regular Season | Saturday, 14/06/1986 | Caulfield City - Maribyrnong Polonia | 3:2 | ||||||
| Regular Season | Saturday, 21/06/1986 | Caulfield City - Morwell Falcons | 2:4 | ||||||
| Regular Season | Saturday, 28/06/1986 | Northcote City - Caulfield City | 3:1 | ||||||
| Regular Season | Saturday, 05/07/1986 | Caulfield City - Western Suburbs | 2:0 | ||||||
| Regular Season | Sunday, 13/07/1986 | Croydon City - Caulfield City | 2:1 | ||||||
| Regular Season | Sunday, 20/07/1986 | Ringwood City - Caulfield City | 0:0 | ||||||
| Regular Season | Saturday, 26/07/1986 | Caulfield City - Springvale City | 2:1 | ||||||
| Regular Season | Saturday, 02/08/1986 | St Albans - Caulfield City | 1:0 | ||||||
| Regular Season | Saturday, 09/08/1986 | Caulfield City - Thomastown | 1:1 | ||||||
| Regular Season | Saturday, 16/08/1986 | Frankston Pines - Caulfield City | 2:1 | ||||||
| Regular Season | Saturday, 23/08/1986 | Caulfield City - Box Hill | 3:1 | ||||||
| Regular Season | Saturday, 30/08/1986 | Melbourne - Caulfield City | 0:1 | ||||||
| Regular Season | Saturday, 06/09/1986 | Caulfield City - Fawkner | 1:3 | ||||||
| Regular Season | Sunday, 14/09/1986 | Maribyrnong Polonia - Caulfield City | 2:1 |