| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | First XI | 1999-10-09 | Murrumbeena | lost to | Hoppers Crossing |
| 8/161 T Lamb 44 K Jayasuriya 28 C Dutton 37* | | 4/200 A Paton 3/72 |
| 2 | First XI | 1999-10-16 | St Johns/St Bedes | drew | Murrumbeena |
| 171 A Paton 7/47 I Jumar 2/41 | | 8/99 T Lamb 27 K Jayasuriya 31* |
| 3 | First XI | 1999-10-30 | Murrumbeena | drew | Highett |
| | | 9/271 S Hay 2/68 L Hardham 2/26 A Paton 2/56 I Jumar 3/56 |
| 5 | Second XI | 1999-11-27 | Beaumaris | def | Murrumbeena |
| 272 G Hay 5/75 D Allamby 2/24
and 6/67 T Lamb 2/6 G Hay 2/25 D Allamby 2/34 | | 118 P Hay 51 John Hindmarsh 27 |
| 6 | Second XI | 1999-12-18 | Murrumbeena |  | North Caulfield Glenhuntly |
| 6/134 C Dutton 30 D Hardham 52* R Breddy 29* | | 9/111 R Breddy 5/54 A Yusuf 3/42 |
| 7 | Second XI | 2000-01-08 | Keilor | def | Murrumbeena |
| 3/179 | | 26
and 2/13 |
