| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | Fourth XI | 1999-10-09 | Murrumbeena | lost to | Ormond |
| 6/145 G Rogers 27 J Gange 32* | | 9/166 M Favre 3/51 B Hardham 4/39 |
| 2 | Second XI | 1999-10-16 | Murrumbeena | lost to | St Johns/St Bedes |
| 124 G Hay 41 P Hay 25 A Price 29 | | 5/233 G Hay 2/57 J Morton 2/37
and 3/24 P Hay 3/11 |
| 3 | Second XI | 1999-10-30 | Highett | drew | Murrumbeena |
| 162 M Favre 4/34 R Breddy 2/35 | | 0/2 |
| 4 | Second XI | 1999-11-13 | Murrumbeena | tied | Avondale Heights |
| 199 A Price 70 G Hay 27 | | 199 R Breddy 8/39 |
| 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 |
| 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 |
| 11 | Second XI | 2000-03-04 | Murrumbeena | lost to | Old Essendon Grammarians |
| 74 | | 4/230 |
