| 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* |
| 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 |
| 5 | Fourth XI | 1999-11-27 | Murrumbeena | | Maccabi Ajax |
| 7/287 S Goold 65 S McDonell 88 B Hardham 32 D Murchie 29 M McRae 32* | | 8/255 S Goold 2/37 J Gange 2/55 J Vardy 2/66 |
| 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 |
| 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* |
