| 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 | 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 |
| 8 | Second XI | 2000-01-15 | Murrumbeena | lost to | Watsonia |
| 89 D Hardham 28
and 138 D Hardham 73 | | 97 P Hay 2/24 D Hardham 4/15
and 5/131 D Hardham 2/23 J Morton 2/27 |
| 9 | First XI | 2000-01-29 | Youlden - Parkville | | Murrumbeena |
| 148 L Hardham 5/15 A Yusuf 3/36 | | 9/175 K Jayasuriya 102* |
| 10 | First XI | 2000-02-19 | Murrumbeena | lost to | MHSOB |
| 90 | | 8/160 A Paton 4/50 A Yusuf 2/18
and 4/46 D Allamby 4/9 |
| 11 | Second XI | 2000-03-04 | Murrumbeena | lost to | Old Essendon Grammarians |
| 74 | | 4/230 |
