| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 2 | Fourth XI | 1999-10-23 | Middle Park |  | Murrumbeena |
| 6/116 D Allamby 3/46 J Vardy 2/29 | | 5/179 G Rogers 48 D Allamby 77* |
| 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 | 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 | First XI | 1999-12-18 | North Caulfield Glenhuntly | def | Murrumbeena |
| 5/144 A Paton 2/59 | | 7/125 S Hay 29 |
| 7 | First XI | 2000-01-08 | Murrumbeena | lost to | Keilor |
| 6/135 S Hay 28 T Lamb 33 K Jayasuriya 31 | | 5/157 D Allamby 2/70 A Paton 2/50 |
| 8 | First XI | 2000-01-15 | Watsonia | | Murrumbeena |
| 70 D Allamby 5/31 A Paton 5/26 | | 113 K Jayasuriya 29
and 4/84 W Dutton 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 | First XI | 2000-03-04 | Old Essendon Grammarians | def | Murrumbeena |
| 180 G Hay 2/20 D Allamby 5/79
and 0/8 | | 89 |
