| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | Third XI | 1999-10-03 | Moorabbin Park | drew | Murrumbeena |
| 167 J Morton 5/44 M Sperling 3/8 | | 1/18 |
| 3 | Third XI | 1999-10-30 | Highett |  | Murrumbeena |
| 43 B Gillespie 5/17 P Gyi 2/13 | | 75
and 0/37 |
| 4 | Third XI | 1999-11-13 | Murrumbeena | | Middle Park |
| 8/244 John Hindmarsh 85 I Walker 50
and 4/62 J Seal 29* | | 166 B Connor 2/26 P Gyi 3/46 J Morton 2/46 |
| 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 |
| 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 | Third XI | 2000-01-29 | East Malvern | def | Murrumbeena |
| 6/204 M Sperling 2/32 S Goold 2/29 | | 83
and 6/38 |
| 10 | Third XI | 2000-02-20 | Murrumbeena | lost to | Carnegie |
| 66 | | 7/193 B Gillespie 3/46 |
| 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* |
