| 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 |
| 4 | First XI | 1999-11-13 | Avondale Heights |  | Murrumbeena |
| 163 S Hay 4/36 A Paton 4/54 | | 4/219 L Hardham 126* S Hay 43 |
| 5 | First XI | 1999-11-27 | Murrumbeena | | Beaumaris |
| 219 W Dutton 41 S Hay 82 K Jayasuriya 59*
and 6/98 A Wood 41 | | 203 R Breddy 2/37 A Paton 5/82 I Jumar 3/53 |
| 6 | First XI | 1999-12-18 | North Caulfield Glenhuntly | def | Murrumbeena |
| 5/144 A Paton 2/59 | | 7/125 S Hay 29 |
| 9 | Second XI | 2000-01-29 | Murrumbeena | lost to | Youlden - Parkville |
| 148 G Hay 37 A Trevethan 37
and 0/22 | | 260 G Hay 3/58 B Hardham 3/64 R Breddy 2/48 |
| 10 | Second XI | 2000-02-12 | MHSOB | def | Murrumbeena |
| 6/174 R Breddy 4/43 | | 9/165 P Hay 49 I Walker 32 J Seal 29 |
