| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 3 | Fourth XI | 1999-10-30 | Murrumbeena | drew | Clayton District |
| 164 D Murchie 31 | | 6/33 J Gange 3/11 J Vardy 3/18 |
| 4 | Fourth XI | 1999-11-13 | Cheltenham |  | Murrumbeena |
| 84 B Hardham 2/26 J Gange 3/16 J Vardy 4/30
and 7/137 | | 213 G Rogers 52 J Gange 31 M McRae 31 |
| 6 | Third XI | 1999-12-18 | Murrumbeena | lost to | Clayton District |
| 6/106 J Seal 46* | | 8/255 M Sperling 3/50 B Gillespie 2/43 |
| 7 | Third XI | 2000-01-08 | Parkdale United | def | Murrumbeena |
| 9/129 M Sperling 2/18 S Goold 2/45 | | 115 D McDermott 27 M Sperling 27 |
| 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 | Third XI | 2000-01-29 | East Malvern | def | Murrumbeena |
| 6/204 M Sperling 2/32 S Goold 2/29 | | 83
and 6/38 |
| 11 | Second XI | 2000-03-04 | Murrumbeena | lost to | Old Essendon Grammarians |
| 74 | | 4/230 |
