| 02 Oct 1999 | | Camberwell Magpies v St Kilda | Camberwell Sports Ground, Melbourne | Results |
| 02 Oct 1999 | | Dandenong v University | Shepley Oval, Melbourne | Results |
| 02 Oct 1999 | | Fitzroy-Doncaster v Richmond | Schramm's Reserve, Melbourne | Results |
| 02 Oct 1999 | | Geelong v Northcote | Geelong Cricket Ground, Geelong | Results |
| 02 Oct 1999 | | Melbourne v Frankston Peninsula | Albert Ground, Melbourne | Results |
| 02 Oct 1999 | | North Melbourne v Hawthorn-Waverley | Showgrounds, Cobram | Results |
| 02 Oct 1999 | | Prahran v Footscray | Toorak Park, Melbourne | Results |
| 02 Oct 1999 | | Ringwood v Essendon | Jubilee Park, Ringwood, Melbourne | Results |
| 02 Oct 1999 | | South Melbourne v Carlton | Harry Trott Oval, Melbourne | Results |
| 09 Oct 1999 | | Carlton v Ringwood | Princes Park, Melbourne | Results |
| 09 Oct 1999 | | Essendon v Prahran | Windy Hill, Melbourne | Results |
| 09 Oct 1999 | | Footscray v North Melbourne | Mervyn G Hughes Oval, Melbourne | Results |
| 09 Oct 1999 | | Frankston Peninsula v Geelong | AH Butler Oval, Melbourne | Results |
| 09 Oct 1999 | | Hawthorn-Waverley v Melbourne | Central Reserve, Melbourne | Results |
| 09 Oct 1999 | | Northcote v Fitzroy-Doncaster | Bill Lawry Oval, Melbourne | Results |
| 09 Oct 1999 | | Richmond v Camberwell Magpies | Richmond Cricket Ground, Melbourne | Results |
| 09 Oct 1999 | | South Melbourne v Dandenong | Harry Trott Oval, Melbourne | Results |
| 09 Oct 1999 | | University v St Kilda | University Oval, Melbourne | Results |
| 16 Oct 1999 | | Camberwell Magpies v Northcote | Camberwell Sports Ground, Melbourne | Results |
| 16 Oct 1999 | | Fitzroy-Doncaster v Frankston Peninsula | Schramm's Reserve, Melbourne | Results |
| 16 Oct 1999 | | Geelong v Hawthorn-Waverley | Geelong Cricket Ground, Geelong | Results |
| 16 Oct 1999 | | Melbourne v Footscray | Albert Ground, Melbourne | Results |
| 16 Oct 1999 | | North Melbourne v Essendon | North Melbourne Cricket Ground, Melbourne | Results |
| 16 Oct 1999 | | Prahran v Carlton | Toorak Park, Melbourne | Results |
| 16 Oct 1999 | | Ringwood v South Melbourne | Jubilee Park, Ringwood, Melbourne | Results |
| 16 Oct 1999 | | St Kilda v Dandenong | St Kilda Cricket Ground, Melbourne | Results |
| 16 Oct 1999 | | University v Richmond | University Oval, Melbourne | Results |
| 30 Oct 1999 | | Carlton v North Melbourne | Princes Park, Melbourne | Results |
| 30 Oct 1999 | | Dandenong v Ringwood | Shepley Oval, Melbourne | Results |
| 30 Oct 1999 | | Essendon v Melbourne | Windy Hill, Melbourne | Results |
| 30 Oct 1999 | | Footscray v Geelong | Mervyn G Hughes Oval, Melbourne | Results |
| 30 Oct 1999 | | Frankston Peninsula v Camberwell Magpies | AH Butler Oval, Melbourne | Results |
| 30 Oct 1999 | | Hawthorn-Waverley v Fitzroy-Doncaster | Central Reserve, Melbourne | Results |
| 30 Oct 1999 | | Northcote v University | Bill Lawry Oval, Melbourne | Results |
| 30 Oct 1999 | | Richmond v St Kilda | Richmond Cricket Ground, Melbourne | Results |
| 30 Oct 1999 | | South Melbourne v Prahran | Harry Trott Oval, Melbourne | Results |
| 02 Nov 1999 | | Camberwell Magpies v Hawthorn-Waverley | Camberwell Sports Ground, Melbourne | Results |
| 02 Nov 1999 | | Melbourne v Carlton | Albert Ground, Melbourne | Results |
| 02 Nov 1999 | | Geelong v Essendon | Geelong Cricket Ground, Geelong | Results |
| 02 Nov 1999 | | Fitzroy-Doncaster v Footscray | Schramm's Reserve, Melbourne | Results |
| 02 Nov 1999 | | North Melbourne v South Melbourne | North Melbourne Cricket Ground, Melbourne | Results |
| 02 Nov 1999 | | Prahran v Ringwood | Toorak Park, Melbourne | Results |
| 02 Nov 1999 | | Richmond v Dandenong | Richmond Cricket Ground, Melbourne | Results |
| 02 Nov 1999 | | St Kilda v Northcote | St Kilda Cricket Ground, Melbourne | Results |
| 02 Nov 1999 | | University v Frankston Peninsula | University Oval, Melbourne | Results |
| 13 Nov 1999 | | Carlton v Geelong | Princes Park, Melbourne | Results |
| 13 Nov 1999 | | Dandenong v Prahran | Shepley Oval, Melbourne | Results |
| 13 Nov 1999 | | Essendon v Fitzroy-Doncaster | Windy Hill, Melbourne | Results |
| 13 Nov 1999 | | Footscray v Camberwell Magpies | Mervyn G Hughes Oval, Melbourne | Results |
| 13 Nov 1999 | | Frankston Peninsula v St Kilda | AH Butler Oval, Melbourne | Results |
| 13 Nov 1999 | | Hawthorn-Waverley v University | Central Reserve, Melbourne | Results |
| 13 Nov 1999 | | Northcote v Richmond | Bill Lawry Oval, Melbourne | Results |
| 13 Nov 1999 | | Ringwood v North Melbourne | Jubilee Park, Ringwood, Melbourne | Results |
| 13 Nov 1999 | | South Melbourne v Melbourne | Harry Trott Oval, Melbourne | Results |
| 20 Nov 1999 | | Camberwell Magpies v Essendon | Camberwell Sports Ground, Melbourne | Results |
| 20 Nov 1999 | | Fitzroy-Doncaster v Carlton | Schramm's Reserve, Melbourne | Results |
| 20 Nov 1999 | | Geelong v South Melbourne | Geelong Cricket Ground, Geelong | Results |
| 20 Nov 1999 | | Melbourne v Ringwood | Albert Ground, Melbourne | Results |
| 20 Nov 1999 | | North Melbourne v Prahran | North Melbourne Cricket Ground, Melbourne | Results |
| 20 Nov 1999 | | Northcote v Dandenong | Bill Lawry Oval, Melbourne | Results |
| 20 Nov 1999 | | Richmond v Frankston Peninsula | Richmond Cricket Ground, Melbourne | Results |
| 20 Nov 1999 | | St Kilda v Hawthorn-Waverley | St Kilda Cricket Ground, Melbourne | Results |
| 20 Nov 1999 | | University v Footscray | University Oval, Melbourne | Results |
| 04 Dec 1999 | | Carlton v Camberwell Magpies | Princes Park, Melbourne | Results |
| 04 Dec 1999 | | Dandenong v North Melbourne | Shepley Oval, Melbourne | Results |
| 04 Dec 1999 | | Essendon v University | Windy Hill, Melbourne | Results |
| 04 Dec 1999 | | Footscray v St Kilda | Mervyn G Hughes Oval, Melbourne | Results |
| 04 Dec 1999 | | Frankston Peninsula v Northcote | AH Butler Oval, Melbourne | Results |
| 04 Dec 1999 | | Hawthorn-Waverley v Richmond | Central Reserve, Melbourne | Results |
| 04 Dec 1999 | | Prahran v Melbourne | Toorak Park, Melbourne | Results |
| 04 Dec 1999 | | Ringwood v Geelong | Jubilee Park, Ringwood, Melbourne | Results |
| 04 Dec 1999 | | South Melbourne v Fitzroy-Doncaster | Harry Trott Oval, Melbourne | Results |
| 18 Dec 1999 | | Camberwell Magpies v South Melbourne | Camberwell Sports Ground, Melbourne | Results |
| 18 Dec 1999 | | Fitzroy-Doncaster v Ringwood | Schramm's Reserve, Melbourne | Results |
| 18 Dec 1999 | | Frankston Peninsula v Dandenong | AH Butler Oval, Melbourne | Results |
| 18 Dec 1999 | | Geelong v Prahran | Geelong Cricket Ground, Geelong | Results |
| 18 Dec 1999 | | Melbourne v North Melbourne | Albert Ground, Melbourne | Results |
| 18 Dec 1999 | | Northcote v Hawthorn-Waverley | Bill Lawry Oval, Melbourne | Results |
| 18 Dec 1999 | | Richmond v Footscray | Richmond Cricket Ground, Melbourne | Results |
| 18 Dec 1999 | | St Kilda v Essendon | St Kilda Cricket Ground, Melbourne | Results |
| 18 Dec 1999 | | University v Carlton | University Oval, Melbourne | Results |
| 08 Jan 2000 | | Carlton v St Kilda | Deakin Reserve, Shepparton | Results |
| 08 Jan 2000 | | Dandenong v Melbourne | Burrage Reserve, Newborough | Results |
| 08 Jan 2000 | | Essendon v Richmond | Kings Park Recreation Reserve, Seymour | Results |
| 08 Jan 2000 | | Footscray v Northcote | Queen Elizabeth II Oval, Bendigo | Results |
| 08 Jan 2000 | | Hawthorn-Waverley v Frankston Peninsula | Wy Yung Oval, Bairnsdale | Results |
| 08 Jan 2000 | | North Melbourne v Geelong | WJ Findlay City Oval, Wangaratta | Results |
| 08 Jan 2000 | | Prahran v Fitzroy-Doncaster | North Ballarat Oval, Ballarat | Results |
| 08 Jan 2000 | | Ringwood v Camberwell Magpies | Princes Park, Maryborough | Results |
| 08 Jan 2000 | | South Melbourne v University | Traralgon Showground, Traralgon | Results |
| 15 Jan 2000 | | Camberwell Magpies v Prahran | Camberwell Sports Ground, Melbourne | Results |
| 15 Jan 2000 | | Fitzroy-Doncaster v North Melbourne | Schramm's Reserve, Melbourne | Results |
| 15 Jan 2000 | | Frankston Peninsula v Footscray | AH Butler Oval, Melbourne | Results |
| 15 Jan 2000 | | Geelong v Melbourne | Geelong Cricket Ground, Geelong | Results |
| 15 Jan 2000 | | Hawthorn-Waverley v Dandenong | Central Reserve, Melbourne | Results |
| 15 Jan 2000 | | Northcote v Essendon | Bill Lawry Oval, Melbourne | Results |
| 15 Jan 2000 | | Richmond v Carlton | Richmond Cricket Ground, Melbourne | Results |
| 15 Jan 2000 | | St Kilda v South Melbourne | St Kilda Cricket Ground, Melbourne | Results |
| 15 Jan 2000 | | University v Ringwood | University Oval, Melbourne | Results |
| 26 Jan 2000 | | Carlton v Northcote | Princes Park, Melbourne | Results |
| 26 Jan 2000 | | Dandenong v Geelong | Shepley Oval, Melbourne | Results |
| 26 Jan 2000 | | Essendon v Frankston Peninsula | Windy Hill, Melbourne | Results |
| 26 Jan 2000 | | Footscray v Hawthorn-Waverley | Mervyn G Hughes Oval, Melbourne | Results |
| 26 Jan 2000 | | Melbourne v Fitzroy-Doncaster | Albert Ground, Melbourne | Results |
| 26 Jan 2000 | | North Melbourne v Camberwell Magpies | North Melbourne Cricket Ground, Melbourne | Results |
| 26 Jan 2000 | | Prahran v University | Princes Park, Maryborough | Results |
| 26 Jan 2000 | | Ringwood v St Kilda | Jubilee Park, Ringwood, Melbourne | Results |
| 26 Jan 2000 | | South Melbourne v Richmond | Harry Trott Oval, Melbourne | Results |
| 29 Jan 2000 | | Camberwell Magpies v Melbourne | Camberwell Sports Ground, Melbourne | Results |
| 29 Jan 2000 | | Fitzroy-Doncaster v Geelong | Schramm's Reserve, Melbourne | Results |
| 29 Jan 2000 | | Footscray v Dandenong | Mervyn G Hughes Oval, Melbourne | Results |
| 29 Jan 2000 | | Frankston Peninsula v Carlton | AH Butler Oval, Melbourne | Results |
| 29 Jan 2000 | | Hawthorn-Waverley v Essendon | Central Reserve, Melbourne | Results |
| 29 Jan 2000 | | Northcote v South Melbourne | Bill Lawry Oval, Melbourne | Results |
| 29 Jan 2000 | | Richmond v Ringwood | Richmond Cricket Ground, Melbourne | Results |
| 29 Jan 2000 | | St Kilda v Prahran | St Kilda Cricket Ground, Melbourne | Results |
| 29 Jan 2000 | | University v North Melbourne | University Oval, Melbourne | Results |
| 12 Feb 2000 | | Carlton v Hawthorn-Waverley | Princes Park, Melbourne | Results |
| 12 Feb 2000 | | Dandenong v Fitzroy-Doncaster | Shepley Oval, Melbourne | Results |
| 12 Feb 2000 | | Essendon v Footscray | Windy Hill, Melbourne | Results |
| 12 Feb 2000 | | Geelong v Camberwell Magpies | Geelong Cricket Ground, Geelong | Results |
| 12 Feb 2000 | | Melbourne v University | Albert Ground, Melbourne | Results |
| 12 Feb 2000 | | North Melbourne v St Kilda | North Melbourne Cricket Ground, Melbourne | Results |
| 12 Feb 2000 | | Prahran v Richmond | Toorak Park, Melbourne | Results |
| 12 Feb 2000 | | Ringwood v Northcote | Jubilee Park, Ringwood, Melbourne | Results |
| 12 Feb 2000 | | South Melbourne v Frankston Peninsula | Harry Trott Oval, Melbourne | Results |
| 19 Feb 2000 | | Camberwell Magpies v Fitzroy-Doncaster | Camberwell Sports Ground, Melbourne | Results |
| 19 Feb 2000 | | Essendon v Dandenong | Windy Hill, Melbourne | Results |
| 19 Feb 2000 | | Footscray v Carlton | Mervyn G Hughes Oval, Melbourne | Results |
| 19 Feb 2000 | | Frankston Peninsula v Ringwood | AH Butler Oval, Melbourne | Results |
| 19 Feb 2000 | | Hawthorn-Waverley v South Melbourne | Central Reserve, Melbourne | Results |
| 19 Feb 2000 | | Northcote v Prahran | Bill Lawry Oval, Melbourne | Results |
| 19 Feb 2000 | | Richmond v North Melbourne | Richmond Cricket Ground, Melbourne | Results |
| 19 Feb 2000 | | St Kilda v Melbourne | St Kilda Cricket Ground, Melbourne | Results |
| 19 Feb 2000 | | University v Geelong | University Oval, Melbourne | Results |
| 04 Mar 2000 | | Carlton v Essendon | Princes Park No 1 Oval, Melbourne | Results |
| 04 Mar 2000 | | Dandenong v Camberwell Magpies | Shepley Oval, Melbourne | Results |
| 04 Mar 2000 | | Fitzroy-Doncaster v University | Schramm's Reserve, Melbourne | Results |
| 04 Mar 2000 | | Geelong v St Kilda | Geelong Cricket Ground, Geelong | Results |
| 04 Mar 2000 | | Melbourne v Richmond | Albert Ground, Melbourne | Results |
| 04 Mar 2000 | | North Melbourne v Northcote | North Melbourne Cricket Ground, Melbourne | Results |
| 04 Mar 2000 | | Prahran v Frankston Peninsula | Toorak Park, Melbourne | Results |
| 04 Mar 2000 | | Ringwood v Hawthorn-Waverley | Jubilee Park, Ringwood, Melbourne | Results |
| 04 Mar 2000 | | South Melbourne v Footscray | Harry Trott Oval, Melbourne | Results |
| 11 Mar 2000 | | Carlton v Dandenong | Princes Park No 1 Oval, Melbourne | Results |
| 11 Mar 2000 | | Essendon v South Melbourne | Windy Hill, Melbourne | Results |
| 11 Mar 2000 | | Fitzroy-Doncaster v St Kilda | Schramm's Reserve, Melbourne | Results |
| 11 Mar 2000 | | Footscray v Ringwood | Mervyn G Hughes Oval, Melbourne | Results |
| 11 Mar 2000 | | Frankston Peninsula v North Melbourne | AH Butler Oval, Melbourne | Results |
| 11 Mar 2000 | | Hawthorn-Waverley v Prahran | Central Reserve, Melbourne | Results |
| 11 Mar 2000 | | Northcote v Melbourne | Bill Lawry Oval, Melbourne | Results |
| 11 Mar 2000 | | Richmond v Geelong | Richmond Cricket Ground, Melbourne | Results |
| 11 Mar 2000 | | University v Camberwell Magpies | University Oval, Melbourne | Results |
| 18 Mar 2000 | Qualifying Final | Hawthorn-Waverley v Melbourne | Central Reserve, Melbourne | Results |
| 18 Mar 2000 | Qualifying Final | Richmond v Fitzroy-Doncaster | Richmond Cricket Ground, Melbourne | Results |
| 18 Mar 2000 | Qualifying Final | St Kilda v Camberwell Magpies | St Kilda Cricket Ground, Melbourne | Results |
| 25 Mar 2000 | Semi-Final | Richmond v Hawthorn-Waverley | Richmond Cricket Ground, Melbourne | Results |
| 25 Mar 2000 | Semi-Final | St Kilda v Melbourne | St Kilda Cricket Ground, Melbourne | Results |
| 31 Mar 2000 | Final | Melbourne v Richmond | Albert Ground, Melbourne | Results |
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