| 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 | Third XI | 1999-10-16 | Murrumbeena | lost to | Ormond |
| 69 | | 213 B Hardham 2/31 B Gillespie 3/34 P Gyi 2/52
and 9/83 S Goold 3/12 J McArthur 2/26 P Gyi 2/22 M Goold 2/16 |
| 3 | Third XI | 1999-10-30 | Highett |  | Murrumbeena |
| 43 B Gillespie 5/17 P Gyi 2/13 | | 75
and 0/37 |
| 5 | Third XI | 1999-11-27 | Springvale | | Murrumbeena |
| 118 P Way 4/4 B Connor 3/10
and 4/100 J Morton 3/8 | | 151 J Gray 33 M Sperling 34 |
| 6 | Third XI | 1999-12-18 | Murrumbeena | lost to | Clayton District |
| 6/106 J Seal 46* | | 8/255 M Sperling 3/50 B Gillespie 2/43 |
| 7 | Third XI | 2000-01-08 | Parkdale United | def | Murrumbeena |
| 9/129 M Sperling 2/18 S Goold 2/45 | | 115 D McDermott 27 M Sperling 27 |
| 8 | Third XI | 2000-01-16 | Murrumbeena | lost to | Cheltenham |
| 90 S Goold 27
and 80 | | 9/97 B Connor 6/37 S Goold 2/18
and 2/75 |
