| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | Second XI | 1999-10-02 | Hoppers Crossing | def | Murrumbeena |
| 5/70 I Walker 2/12
and 3/52 J Rivett 2/31 | | 39
and 80 E Martin 25* |
| 2 | Second XI | 1999-10-16 | Murrumbeena | lost to | St Johns/St Bedes |
| 124 G Hay 41 P Hay 25 A Price 29 | | 5/233 G Hay 2/57 J Morton 2/37
and 3/24 P Hay 3/11 |
| 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 |
| 10 | Third XI | 2000-02-20 | Murrumbeena | lost to | Carnegie |
| 66 | | 7/193 B Gillespie 3/46 |
| 11 | Third XI | 2000-03-05 | Murrumbeena | lost to | Bentleigh |
| 8/88 M Sperling 39 | | 3/220 |
