| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 2 | Third XI | 1999-10-16 | Murrumbeena | lost to | Ormond |
| 69 | | 213 B Hardham 2/31 B Gillespie 3/34 P Gyi 2/52
and 9/83 S Goold 3/12 J McArthur 2/26 P Gyi 2/22 M Goold 2/16 |
| 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 |
| 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 | 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 | 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 | 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 |
