| Rnd | Match Date | Home Team | Result | Away Team |
|---|
| 1 | 1999-10-16 | Murrumbeena | lost to | East Malvern |
| 33 | | 6/84 R Tate 2/5 L Grant 2/2 |
| 2 | 1999-10-23 | Glen Waverley Church of Christ | def | Murrumbeena |
| 6/91 JN Banks 2/6 T Garde 2/19 | | 21 |
| 3 | 1999-10-31 | Notting Hill-Brandon Park | def | Murrumbeena |
| 7/158 D Hay 2/16
and 0/ | | 98 L Grant 53* |
| 4 | 1999-11-12 | Murrumbeena | lost to | Oak Dist Foot/Princes Park |
| 76 JN Banks 29*
and 3/37 | | 207 JN Banks 2/8 J Lockhart 2/12 |
| 5 | 1999-11-25 | Murrumbeena | lost to | East Malvern Blue |
| 7/162 JN Banks 47* L Grant 45* | | 193 M Smith 2/24 P Hussey 2/29 D Hay 2/12 |
| 6 | 1999-12-10 | Mt Waverley/Mayfield White | def | Murrumbeena |
| 2/127 | | 5/71 T Newton 25N |
| 7 | 1999-12-17 | St Pauls Amsleigh Park | def | Murrumbeena |
| 3/111 L McDonell 2/11 | | 6/92 J Lockhart 25N JN Banks 26N |
| 8 | 2000-01-21 | Murrumbeena | lost to | Glen Waverley Gold |
| 5/132 JN Banks 27N J Lockhart 25N | | 3/133 T McDonell 2/18 |
| 9 | 2000-01-28 | Glen Waverley Green |  | Murrumbeena |
| 9/161 N Jeffery 2/16 R Tate 2/8 | | 8/176 R Tate 25* |
| 10 | 2000-02-11 | Murrumbeena | lost to | Clayton District |
| 109 R Tate 31* | | 7/207 |
| 11 | 2000-02-25 | Murrumbeena | lost to | Mt Waverley Mayfield Green |
| 8/65 | | 1/116 |
