1999 ‘A’ Grade Senior Men’s results:
| Round | Club Name | Score | Club Name | Score | Notes | |
| 1 | Strathmore | 21.5.131 | d | Oak Park | 13.15.93 | |
| 2 | Doutta Stars | 20.12.132 | d | Oak Park | 10.11.71 | |
| 3 | Keilor Park | 16.13.109 | d | Oak Park | 15.7.97 | |
| 4 | Airport West | 24.12.156 | d | Oak Park | 11.7.73 | |
| 5 | Keilor | 17.13.115 | d | Oak Park | 11.7.73 | |
| 6 | Aberfeldie | 11.12.78 | d | Oak Park | 4.6.30 | |
| 7 | Oak Park | 14.9.93 | d | East Keilor | 10.9.69 | |
| 8 | Oak Park | 15.12.102 | d | West Coburg | 1.8.14 | |
| 9 | Avondale Heights | 11.11.77 | d | Oak Park | 0.16.16 | |
| 10 | Oak Park | 18.7.115 | d | Strathmore | 17.9.111 | |
| 11 | Doutta Stars | 17.13.115 | d | Oak Park | 10.7.67 | |
| 12 | Oak Park | 14.10.94 | d | Keilor Park | 13.12.90 | |
| 13 | Airport West | 25.12.162 | d | Oak Park | 14.8.92 | |
| 14 | Keilor | 12.22.94 | d | Oak Park | 4.11.35 | |
| 15 | Oak Park | 15.13.103 | d | Aberfeldie | 12.10.82 | |
| 16 | Oak Park | 20.17.137 | d | East Keilor | 18.8.116 | |
| 17 | Oak Park | 10.19.79 | d | West Coburg | 9.8.62 | |
| 18 | Avondale Heights | 6.11.47 | d | Oak Park | 6.9.45 |