| Rnd | Match Date | Home Team | Result | Away Team |
|---|
| 1 | 2008-10-11 | Oakleigh Dist Footballers |  | Murrumbeena |
| 6/54 | | 5/85 |
| 2 | 2008-10-18 | Toorak-Prahran Colts | | Murrumbeena |
| 4/75 | | 6/91 |
| 3 | 2008-10-25 | Murrumbeena | | Caulfield Green |
| 2/106 | | 38 C Joyce 2/4 AJ Ross 3/4 |
| 4 | 2008-11-01 | Caulfield Gold | | Murrumbeena |
| 6/54 | | 2/136 |
| 5 | 2008-11-08 | Murrumbeena | | Mt Waverley White |
| 6/73 | | 2/51 |
| 6 | 2008-11-15 | Glen Waverley | | Murrumbeena |
| 7/31 B Chapman 2/3 | | 5/90 |
| 7 | 2008-11-22 | Murrumbeena | no play | Clayton District |
| 8 | 2008-11-29 | Murrumbeena | lost to | Mt Waverley Mayfield |
| 5/73 | | 4/91 |
| 9 | 2008-12-06 | Emmanuel Sth Oakleigh | def | Murrumbeena |
| 5/107 | | 7/68 |
| 10 | 2008-12-13 | Murrumbeena | no play | Toorak-Prahran Gold |
| 11 | 2008-12-20 | Mt Waverley Mayfield | | Murrumbeena |
| 35 AR Ross 2/3 C Joyce 2/1 | | 2/136 S Holzer 27N |
| 12 | 2009-01-17 | Oakleigh Dist Footballers | | Murrumbeena |
| 5/91 H Boontjes 2/5 E Faragher 2/7 | | 4/121 M Mahoney 25N |
| 13 | 2009-01-24 | Murrumbeena | | Toorak-Prahran Colts |
| 4/112 | | 8/79 B Joyce 2/8 H Boontjes 2/7 |
| 14 | 2009-01-31 | Caulfield Green | | Murrumbeena |
| 9/139 H Boontjes 2/8 C Joyce 2/5 | | 3/168 O Munn 25N AR Ross 25N |
| 15 | 2009-02-07 | Murrumbeena | no play | Caulfield Gold |
| 16 | 2009-02-14 | Mt Waverley White | | Murrumbeena |
| 7/90 B Chapman 2/5 | | 3/111 |
| 17 | 2009-02-21 | Murrumbeena | | Glen Waverley |
| 5/148 | | 6/43 AR Ross 2/5 |
