| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 3 | Second XI | 1998-10-31 | Highett | def | Murrumbeena |
| 179 P Blum 3/38 P Hay 2/25 R Breddy 3/41 | | 123 A Price 35 |
| 4 | Second XI | 1998-11-21 | Murrumbeena | lost to | Beaumaris |
| 121 C Howard 36 | | 7/203 P Gyi 5/34 |
| 5 | Second XI | 1998-12-05 | Old Essendon Grammarians | def | Murrumbeena |
| 6/169 I Walker 3/66 | | 8/105 |
| 6 | Second XI | 1998-12-12 | Murrumbeena | lost to | Royal Park Brunswick |
| 121 D Hardham 47 | | 155 R Breddy 4/23 P Gyi 2/26 I Jumar 3/53
and 2/32 |
| 7 | Second XI | 1999-01-09 | North Caulfield Glenhuntly | def | Murrumbeena |
| 7/157 G Hay 4/23 | | 9/136 D Hardham 74 |
| 8 | Third XI | 1999-01-16 | Murrumbeena | lost to | Middle Park |
| 4/93 J Seal 34* J Fielder 35* | | 5/168 P Way 4/43 |
| 9 | Third XI | 1999-01-24 | Moorabbin Park |  | Murrumbeena |
| 98 P Way 3/17 L Hancock 4/49 A Loughron 2/4
and 9/124 L Hancock 3/37 A Loughron 4/33 | | 198 J Gray 35 P Way 91 |
