| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | Fourth XI | 1999-10-09 | Murrumbeena | lost to | Ormond |
| 6/145 G Rogers 27 J Gange 32* | | 9/166 M Favre 3/51 B Hardham 4/39 |
| 2 | Fourth XI | 1999-10-23 | Middle Park |  | Murrumbeena |
| 6/116 D Allamby 3/46 J Vardy 2/29 | | 5/179 G Rogers 48 D Allamby 77* |
| 6 | Fourth XI | 1999-12-18 | Highett | def | Murrumbeena |
| 8/159 J Gange 3/25 J Vardy 3/70 | | 7/114 S McDonell 35 |
| 7 | Fourth XI | 2000-01-09 | Murrumbeena | lost to | Springvale |
| 78 | | 99 J Gange 5/24 B Smith 4/14
and 1/33 |
| 8 | Fourth XI | 2000-01-23 | St Johns/St Bedes | def | Murrumbeena |
| 8/132 B Hardham 3/36(inc hat-trick) J Vardy 3/19 | | 130 P Way 26 B Smith 31* |
| 9 | Fourth XI | 2000-01-30 | Murrumbeena | | East Malvern |
| 5/142 G Rogers 31 A Clifton 42 E Martin 27
and 0/31 | | 98 A Clifton 2/11 J Vardy 6/42 J Morton 2/8
and 74 E Martin 2/22 J Guest 3/18 J Vardy 3/33 |
| 11 | Fourth XI | 2000-03-04 | Bentleigh | | Murrumbeena |
| 7/99 J Gange 2/15 J Vardy 3/36 | | 6/199 A Clifton 61 D Murchie 34 B Smith 27* |
