| 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 | First XI | 1999-10-16 | St Johns/St Bedes | drew | Murrumbeena |
| 171 A Paton 7/47 I Jumar 2/41 | | 8/99 T Lamb 27 K Jayasuriya 31* |
| 3 | First XI | 1999-10-30 | Murrumbeena | drew | Highett |
| | | 9/271 S Hay 2/68 L Hardham 2/26 A Paton 2/56 I Jumar 3/56 |
| 4 | Second XI | 1999-11-13 | Murrumbeena | tied | Avondale Heights |
| 199 A Price 70 G Hay 27 | | 199 R Breddy 8/39 |
| 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 |
