| 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 | Second XI | 1999-10-30 | Highett | drew | Murrumbeena |
| 162 M Favre 4/34 R Breddy 2/35 | | 0/2 |
| 4 | Second XI | 1999-11-13 | Murrumbeena | tied | Avondale Heights |
| 199 A Price 70 G Hay 27 | | 199 R Breddy 8/39 |
| 5 | Second XI | 1999-11-27 | Beaumaris | def | Murrumbeena |
| 272 G Hay 5/75 D Allamby 2/24
and 6/67 T Lamb 2/6 G Hay 2/25 D Allamby 2/34 | | 118 P Hay 51 John Hindmarsh 27 |
