| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | Third XI | 1999-10-03 | Moorabbin Park | drew | Murrumbeena |
| 167 J Morton 5/44 M Sperling 3/8 | | 1/18 |
| 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 |
| 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 |
| 8 | Third XI | 2000-01-16 | Murrumbeena | lost to | Cheltenham |
| 90 S Goold 27
and 80 | | 9/97 B Connor 6/37 S Goold 2/18
and 2/75 |
| 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 |
