| Rnd | Team | Match Date | Home Team | Result | Away Team |
|---|
| 2 | Third XI | 1999-10-16 | Murrumbeena | lost to | Ormond |
| 69 | | 213 B Hardham 2/31 B Gillespie 3/34 P Gyi 2/52
and 9/83 S Goold 3/12 J McArthur 2/26 P Gyi 2/22 M Goold 2/16 |
| 3 | Third XI | 1999-10-30 | Highett |  | Murrumbeena |
| 43 B Gillespie 5/17 P Gyi 2/13 | | 75
and 0/37 |
| 4 | Third XI | 1999-11-13 | Murrumbeena | | Middle Park |
| 8/244 John Hindmarsh 85 I Walker 50
and 4/62 J Seal 29* | | 166 B Connor 2/26 P Gyi 3/46 J Morton 2/46 |
| 5 | Third XI | 1999-11-27 | Springvale | | Murrumbeena |
| 118 P Way 4/4 B Connor 3/10
and 4/100 J Morton 3/8 | | 151 J Gray 33 M Sperling 34 |
| 10 | Third XI | 2000-02-20 | Murrumbeena | lost to | Carnegie |
| 66 | | 7/193 B Gillespie 3/46 |
| 11 | Third XI | 2000-03-05 | Murrumbeena | lost to | Bentleigh |
| 8/88 M Sperling 39 | | 3/220 |
