| Rnd | Match Date | Home Team | Result | Away Team |
|---|
| 1 | 1999-10-17 | Murrumbeena |  | Toorak Gold |
| 7/137 A Hammer 34 M Sherman 28* | | 5/89 T Hardham 2/8 |
| 2 | 1999-10-24 | The Saints | | Murrumbeena |
| 42 B de Jong 2/6 | | 6/131 B de Jong 31 A Hammer 27 |
| 3 | 1999-10-31 | Maccabi Ajax White | | Murrumbeena |
| 67 C Groarke 2/3 S Dennehy 2/2 S McKenzie 2/13 | | 5/229 A Hammer 50N J McLean 51N C Groarke 26 M Sherman 30
and 3/31 |
| 4 | 1999-11-14 | Murrumbeena | lost to | Toorak Red |
| 76 | | 6/174 Z Goold 2/7 S Dennehy 2/15 B Yeo 2/11 |
| 5 | 1999-11-28 | Murrumbeena | lost to | East Malvern Green |
| 95 M Sherman 35 C Groarke 30 | | 4/162 A Abedin 3/15 |
| 6 | 1999-12-12 | Toorak Blue | def | Murrumbeena |
| 9/128 M Sherman 2/23 | | 6/121 A Hammer 51N |
| 7 | 1999-12-19 | Murrumbeena | | Maccabi Ajax |
| 8/68 | | 5/67 |
| 8 | 2000-01-23 | Murrumbeena | | Bye |
| 9 | 2000-01-30 | Emmanuel | | Murrumbeena |
| 8/129 B de Jong 2/5 | | 8/146 C Groarke 29 A Hammer 28 |
| 10 | 2000-02-13 | Toorak | | Murrumbeena |
| 138 M Sherman 2/12 M Filliponi 2/19 | | 9/165 S McKenzie 30 SHAUN Gange 26* |
| 11 | 2000-02-27 | The Saints | | Murrumbeena |
| 30 M Sherman 4/7 T Hardham 2/7
and 4/44 B van Weel 2/2 | | 4/183 A Hammer 50N M Sherman 50N |
| SF | 2000-03-05 | Toorak Red | def | Murrumbeena |
| 7/194 Z Goold 4/33 | | 93 |
