| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 1 | Fifth XI | 1939-10-07 | Murrumbeena |  | Murrumbeena (D) |
| 198 F Whelan 50 R Brown 36 | | 29 F Whelan 5/19 P Walsh 2/3
and 3/29 |
| 2 | D Team | 1939-10-21 | Murrumbeena | lost to | Murrumbeena Footballers |
| 55
and 65 | | 166 R Saker 3/21 P Walsh 2/22 S Meeks 2/52 |
| 3 | D Team | 1939-11-04 | Murrumbeena | lost to | Trinity |
| 68
and 8/103 A Forscutt 27 R Gillam 31* | | 115 S Meeks 3/21 R Gillam 2/4 R Saker 2/26 |
| 4 | Fifth XI | 1939-11-18 | Murrumbeena ANA | def | Murrumbeena |
| 6/176 J Eakins 2/24 B Brown 3/16 | | 69
and 31 |
| 10 | Fifth XI | 1940-02-10 | Cooper's Social Club | def | Murrumbeena |
| 5/188 E Rowarth 2/31 | | 71
and 14 |
