| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | Fifth XI | 1989-10-07 | Mazenod |  | Murrumbeena |
| 6/50 R Breddy 2/1 A Williams 2/19 | | 4/258 A Loughron 49 J Bailes 148* |
| 3 | Fifth XI | 1989-10-21 | Murrumbeena | | East Oakleigh |
| 8/340 A Loughron 119 R Smale 157 | | 126 J Gange 6/47 L Saville 2/9 R Paton 2/65
and 9/93 A Loughron 6/54 G Burns 2/28 |
| 4 | Fifth XI | 1989-11-04 | Salesian Old Boys | | Murrumbeena |
| 76 J Dent 4/30 J Gange 3/34
and 5/155 V Boyd 2/25 | | 3/146 M Rice 67 A Rigus 57 |
| 5 | Fifth XI | 1989-11-18 | Murrumbeena | | Clayton District |
| 8/182 A Loughron 27 J Dent 49
and 0/21 | | 105 J Dent 2/55 J Gange 2/14 R Paton 6/30
and 93 J Dent 4/46 R Paton 3/45 |
| 6 | Fifth XI | 1989-12-02 | Murrumbeena | lost to | Glen Waverley Hawks |
| 186 N Jamieson 33 Rob Gray 30 J Dent 48 | | 207 J Dent 3/47 S Arnett 3/26 J Gange 2/51 |
| 7 | Fifth XI | 1989-12-16 | Murrumbeena | lost to | St Pauls Glen Waverley |
| 6/151 A Gillbee 63* S Arnett 28 | | 5/175 R Paton 3/28 |
| 8 | Fifth XI | 1990-01-13 | Murrumbeena | | Legend Park |
| 6/290 M Rice 52 Rob Gray 40 I Shaw 88 R Paton 64* | | 279 R Breddy 3/79 J Gange 2/44 R Paton 2/58 |
| 9 | Fifth XI | 1990-01-27 | Mt Waverley Catholics | def | Murrumbeena |
| 291 R Paton 2/14 J Gange 6/108
and 1/35 | | 183 N Jamieson 37 J Dent 67 |
