| Rnd | Match Date | Home Team | Result | Away Team |
|---|
| 1 | 1999-10-17 | East Malvern |  | Murrumbeena |
| 9/121 L Smith 2/5 J McLean 2/7 S Coddington 2/6 | | 4/152 T Lamb 121* |
| 2 | 1999-10-24 | Murrumbeena | | St Johns Elsternwick |
| 7/100 T Lamb 56 | | 6/95 T Lamb 2/10 M Goold 2/22 |
| 3 | 1999-10-31 | Toorak | def | Murrumbeena |
| 7/225 A Roberts 2/30 | | 7/218 JG Banks 85 A Roberts 30* |
| 4 | 1999-11-14 | Emmanuel | | Murrumbeena |
| 62 J McLean 3/13 A Roberts 5/19
and 3/103 D Hogarty 3/16 | | 76 |
| 5 | 1999-11-28 | Murrumbeena | lost to | Maccabi Ajax |
| 68
and 6/65 | | 169 L Smith 2/20 B Hardham 3/40 A Roberts 3/39 |
| 6 | 1999-12-12 | Murrumbeena | lost to | Melbourne High School |
| 7/83 A Roberts 27 | | 4/103 L Smith 2/15 |
| 7 | 1999-12-19 | Maccabi Ajax Blue | | Murrumbeena |
| 64 A Roberts 2/19 L Smith 4/9 | | 5/147 T Lamb 73 J Martin 32* |
| 8 | 2000-01-23 | Murrumbeena | | East Malvern |
| 5/110 A Roberts 41 L Smith 46* | | 66 T Lamb 3/13 A Roberts 3/12 |
| 9 | 2000-01-30 | The Saints | | Murrumbeena |
| 9/115 JG Banks 5/26 A Abedin 2/22 | | 8/219 T Lamb 89 J Martin 27 A Abedin 32* |
| 10 | 2000-02-13 | Toorak | | Murrumbeena |
| 5/184 T Lamb 3/40 | | 8/286 T Lamb 160 L Smith 41* |
| 11 | 2000-02-27 | Murrumbeena | | Emmanuel |
| 4/163 T Lamb 96 | | 8/72 A Roberts 2/11 A Abedin 3/13 |
| SF | 2000-03-05 | Maccabi Ajax | def | Murrumbeena |
| 168 T Lamb 2/31 L Smith 4/38 A Abedin 3/26 | | 156 T Lamb 72 |
