| Rnd | Match Date | Home Team | Result | Away Team |
|---|
| 1 | 1999-10-15 | Central Park Warriors |  | Murrumbeena |
| 7/56 M Hyde 2/4 | | 3/125 T Hardham 44 J McLean 51* |
| 2 | 1999-10-23 | Murrumbeena | | Glen Waverley Church of Christ |
| 2/141 T Hardham 50* J McLean 53* | | 0/107 J McLean 2/9 |
| 3 | 1999-11-05 | Murrumbeena | no play | Notting Hill-Brandon Park |
| 4 | 1999-11-12 | Mt Waverley Harlequins | def | Murrumbeena |
| 7/163 M Rundell 3/17 | | 126 J McLean 58* |
| 5 | 1999-11-26 | Mt Waverley Mayfield | | Murrumbeena |
| 6/164 M Harold 2/16 | | 2/193 C Groarke 50* Z Goold 36 T Hardham 50* |
| 6 | 1999-12-10 | Murrumbeena | | Bye |
| 7 | 1999-12-17 | Murrumbeena | | Central Park Warriors |
| 1/150 M Harold 50* T Hardham 42 J McLean 40* | | 7/81 M Sherman 2/6 M Hyde 2/10 |
| 8 | 2000-01-21 | Salesian College | | Murrumbeena |
| 6/53 C Groarke 2/3 Z Goold 2/5 | | 3/102 T Hardham 51* |
| 9 | 2000-01-28 | Murrumbeena | | Glen Waverley Church of Christ |
| 9/194 J McLean 35 M Harold 53* M Sherman 28 | | 151 J McLean 3/8 Z Goold 3/16 |
| 10 | 2000-02-13 | Murrumbeena | | Notting Hill-Brandon Park |
| 4/142 J McLean 51* T Hardham 38 | | 6/58 |
| 11 | 2000-02-25 | Mt Waverley Harlequins | | Murrumbeena |
| 2/79 | | 3/109 C Groarke 37* T Hardham 27 |
| SF | 2000-03-03 | Murrumbeena | | Mt Waverley Mayfield |
| 7/104 J McLean 30N T Hardham 27N | | 8/60 M Sherman 3/4 |
| GF | 2000-03-17 | Mt Waverley Harlequins | def | Murrumbeena |
| 5/168 T Hardham 2/19 M Harold 2/12 | | 8/118 |
