| Age Group/Div | Round | Date | Time | Home Team | Away Team | Field |
| 10 / U10/2 | 1 | 4/04/2009 | 09:50 | BTH Raiders Soccer Club | Manly Vale Football Club | Wyatt Ave |
| 10 / U10/2 | 2 | 11/04/2009 | 08:20 | Mosman Football Club | Manly Vale Football Club | Alan Border Oval |
| 10 / U10/2 | 3 | 2/05/2009 | 09:50 | Manly Vale Football Club | Curl Curl Youth Club | David Thomas 2 |
| 10 / U10/2 | 4 | 9/05/2009 | 08:20 | Avalon Soccer Club | Manly Vale Football Club | Careel Bay 1 |
| 10 / U10/2 | 5 | 16/05/2009 | 09:50 | Manly Vale Football Club | Seaforth Football Club | David Thomas 2 |
| 10 / U10/2 | 6 | 23/05/2009 | 11:20 | Pittwater RSL Football Club | Manly Vale Football Club | Jackson Road 1 |
| 10 / U10/2 | 7 | 30/05/2009 | 09:50 | Manly Vale Football Club | Collaroy Cromer Strikers Football Club | David Thomas 2 |
| 10 / U10/2 | 8 | 6/06/2009 | 09:50 | Manly Vale Football Club | Forest Killarney Football Club | David Thomas 3 |
| 10 / U10/2 | 9 | 8/06/2009 | 09:50 | Narrabeen Football Club | Manly Vale Football Club | Boondah 1 |
| 10 / U10/2 | 10 | 13/06/2009 | 09:50 | Manly Vale Football Club | BTH Raiders Soccer Club | David Thomas 2 |
| 10 / U10/2 | 11 | 20/06/2009 | 09:50 | Manly Vale Football Club | Mosman Football Club | David Thomas 2 |
| 10 / U10/2 | 12 | 27/06/2009 | 11:20 | Curl Curl Youth Club | Manly Vale Football Club | David Thomas 3 |
| 10 / U10/2 | 13 | 4/07/2009 | 09:50 | Manly Vale Football Club | Avalon Soccer Club | David Thomas 2 |
| 10 / U10/2 | 14 | 11/07/2009 | 09:50 | Seaforth Football Club | Manly Vale Football Club | Seaforth 1 |
| 10 / U10/2 | 15 | 25/07/2009 | 09:50 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 2 |
| 10 / U10/2 | 16 | 1/08/2009 | 09:50 | Collaroy Cromer Strikers Football Club | Manly Vale Football Club | St Matthews 3 |
| 10 / U10/2 | 17 | 8/08/2009 | 09:50 | Forest Killarney Football Club | Manly Vale Football Club | Melwood 1 |
| 10 / U10/2 | 18 | 15/08/2009 | 11:20 | Manly Vale Football Club | Narrabeen Football Club | David Thomas 3 |
| 10 / U10/4 | 1 | 4/04/2009 | 09:50 | Narrabeen Football Club | Manly Vale Football Club | Boondah 2 |
| 10 / U10/4 | 2 | 11/04/2009 | 11:20 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 2 |
| 10 / U10/4 | 3 | 2/05/2009 | 09:50 | Seaforth Football Club | Manly Vale Football Club | Tania Park 2 |
| 10 / U10/4 | 4 | 9/05/2009 | 11:20 | Manly Vale Football Club | Curl Curl Youth Club | Millers 3 |
| 10 / U10/4 | 5 | 16/05/2009 | 09:50 | Brookvale Football Club | Manly Vale Football Club | Passmore 2 |
| 10 / U10/4 | 6 | 30/05/2009 | 11:20 | Manly Vale Football Club | BTH Raiders Soccer Club | David Thomas 2 |
| 10 / U10/4 | 7 | 6/06/2009 | 00:00 | ~~bye~~ | Manly Vale Football Club | |
| 10 / U10/4 | 8 | 13/06/2009 | 11:20 | Manly Vale Football Club | Narrabeen Football Club | David Thomas 2 |
| 10 / U10/4 | 9 | 20/06/2009 | 11:20 | Pittwater RSL Football Club | Manly Vale Football Club | Jackson Road 1 |
| 10 / U10/4 | 10 | 27/06/2009 | 09:50 | Manly Vale Football Club | Seaforth Football Club | David Thomas 3 |
| 10 / U10/4 | 11 | 4/07/2009 | 09:50 | Curl Curl Youth Club | Manly Vale Football Club | Abbott Rd 4 |
| 10 / U10/4 | 12 | 11/07/2009 | 09:50 | Manly Vale Football Club | Brookvale Football Club | David Thomas 3 |
| 10 / U10/4 | 13 | 25/07/2009 | 09:50 | BTH Raiders Soccer Club | Manly Vale Football Club | Wyatt Ave |
| 10 / U10/4 | 14 | 1/08/2009 | 00:00 | Manly Vale Football Club | ~~bye~~ | |
| 10 / U10/6 | 1 | 4/04/2009 | 08:20 | Curl Curl Youth Club | Manly Vale Football Club | Abbott Rd 4 |
| 10 / U10/6 | 2 | 11/04/2009 | 09:50 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 2 |
| 10 / U10/6 | 3 | 2/05/2009 | 09:50 | Harbord Seasiders United Football Club | Manly Vale Football Club | Nolans 4 |
| 10 / U10/6 | 4 | 9/05/2009 | 09:50 | Manly Vale Football Club | Mosman Football Club | Millers 3 |
| 10 / U10/6 | 5 | 16/05/2009 | 11:20 | Seaforth Football Club | Manly Vale Football Club | Tania Park 2 |
| 10 / U10/6 | 6 | 30/05/2009 | 08:20 | Manly Vale Football Club | Avalon Soccer Club | David Thomas 3 |
| 10 / U10/6 | 7 | 6/06/2009 | 11:20 | Collaroy Cromer Strikers Football Club | Manly Vale Football Club | St Matthews 3 |
| 10 / U10/6 | 8 | 13/06/2009 | 11:20 | Manly Vale Football Club | Curl Curl Youth Club | David Thomas 3 |
| 10 / U10/6 | 9 | 20/06/2009 | 09:50 | Pittwater RSL Football Club | Manly Vale Football Club | Jackson Road 2 |
| 10 / U10/6 | 10 | 27/06/2009 | 09:50 | Manly Vale Football Club | Harbord Seasiders United Football Club | David Thomas 2 |
| 10 / U10/6 | 11 | 4/07/2009 | 09:50 | Mosman Football Club | Manly Vale Football Club | Alan Border Oval |
| 10 / U10/6 | 12 | 11/07/2009 | 09:50 | Manly Vale Football Club | Seaforth Football Club | Millers 1 |
| 10 / U10/6 | 13 | 25/07/2009 | 09:50 | Avalon Soccer Club | Manly Vale Football Club | Careel Bay 1 |
| 10 / U10/6 | 14 | 1/08/2009 | 08:20 | Manly Vale Football Club | Collaroy Cromer Strikers Football Club | David Thomas 2 |
| 11 / U11/3 | 1 | 4/04/2009 | 08:20 | Manly Vale Football Club | Seaforth Football Club | David Thomas 2 |
| 11 / U11/3 | 2 | 11/04/2009 | 08:20 | Forest Killarney Football Club | Manly Vale Football Club | Melwood 2 |
| 11 / U11/3 | 3 | 2/05/2009 | 00:00 | Manly Vale Football Club | ~~bye~~ | |
| 11 / U11/3 | 4 | 9/05/2009 | 09:50 | Pittwater RSL Football Club | Manly Vale Football Club | Jackson Road 2 |
| 11 / U11/3 | 5 | 16/05/2009 | 11:20 | Manly Vale Football Club | Beacon Hill Football Club | David Thomas 2 |
| 11 / U11/3 | 6 | 30/05/2009 | 09:50 | Manly Allambie United Football Club | Manly Vale Football Club | Millers 2 |
| 11 / U11/3 | 7 | 6/06/2009 | 09:50 | Manly Vale Football Club | Curl Curl Youth Club | Millers 2 |
| 11 / U11/3 | 8 | 13/06/2009 | 09:50 | Seaforth Football Club | Manly Vale Football Club | Seaforth 2 |
| 11 / U11/3 | 9 | 20/06/2009 | 11:20 | Manly Vale Football Club | Forest Killarney Football Club | David Thomas 2 |
| 11 / U11/3 | 10 | 27/06/2009 | 00:00 | ~~bye~~ | Manly Vale Football Club | |
| 11 / U11/3 | 11 | 4/07/2009 | 11:20 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 2 |
| 11 / U11/3 | 12 | 11/07/2009 | 09:50 | Beacon Hill Football Club | Manly Vale Football Club | Tristram Rd (Beacon Hill High School) |
| 11 / U11/3 | 13 | 25/07/2009 | 11:20 | Manly Vale Football Club | Manly Allambie United Football Club | David Thomas 2 |
| 11 / U11/3 | 14 | 1/08/2009 | 11:20 | Curl Curl Youth Club | Manly Vale Football Club | Abbott Rd 5 |
| 11 / U11/4 | 1 | 4/04/2009 | 09:50 | Manly Vale Football Club | St Augustines Soccer Club A | David Thomas 2 |
| 11 / U11/4 | 2 | 11/04/2009 | 00:00 | ~~bye~~ | Manly Vale Football Club | |
| 11 / U11/4 | 3 | 2/05/2009 | 11:20 | Mosman Football Club | Manly Vale Football Club | Middle Head Oval |
| 11 / U11/4 | 4 | 9/05/2009 | 09:50 | St Augustines Soccer Club B | Manly Vale Football Club | Passmore 1 |
| 11 / U11/4 | 5 | 16/05/2009 | 08:20 | Manly Vale Football Club | Narrabeen Football Club | David Thomas 3 |
| 11 / U11/4 | 6 | 23/05/2009 | 09:50 | Avalon Soccer Club | Manly Vale Football Club | Careel Bay 2 |
| 11 / U11/4 | 7 | 30/05/2009 | 09:50 | Manly Vale Football Club | Wakehurst Football Club | David Thomas 3 |
| 11 / U11/4 | 8 | 6/06/2009 | 11:20 | Pittwater RSL Football Club | Manly Vale Football Club | Kitchener 1 |
| 11 / U11/4 | 9 | 8/06/2009 | 09:50 | Manly Vale Football Club | Beacon Hill Football Club | Millers 2 |
| 11 / U11/4 | 10 | 13/06/2009 | 11:20 | St Augustines Soccer Club A | Manly Vale Football Club | Passmore 1 |
| 11 / U11/4 | 11 | 20/06/2009 | 00:00 | Manly Vale Football Club | ~~bye~~ | |
| 11 / U11/4 | 12 | 27/06/2009 | 11:20 | Manly Vale Football Club | Mosman Football Club | David Thomas 2 |
| 11 / U11/4 | 13 | 4/07/2009 | 08:20 | Manly Vale Football Club | St Augustines Soccer Club B | David Thomas 3 |
| 11 / U11/4 | 14 | 11/07/2009 | 09:50 | Narrabeen Football Club | Manly Vale Football Club | Boondah 2 |
| 11 / U11/4 | 15 | 25/07/2009 | 08:20 | Manly Vale Football Club | Avalon Soccer Club | David Thomas 3 |
| 11 / U11/4 | 16 | 1/08/2009 | 09:50 | Wakehurst Football Club | Manly Vale Football Club | Lionel Watts 3 |
| 11 / U11/4 | 17 | 8/08/2009 | 11:20 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 2 |
| 11 / U11/4 | 18 | 15/08/2009 | 08:20 | Beacon Hill Football Club | Manly Vale Football Club | Beacon Hill Oval 2 |
| 12 / U12/2 | 1 | 4/04/2009 | 11:20 | Forest Killarney Football Club | Manly Vale Football Club | Melwood 1 |
| 12 / U12/2 | 2 | 11/04/2009 | 09:50 | Pittwater RSL Football Club | Manly Vale Football Club | Jackson Road 1 |
| 12 / U12/2 | 3 | 2/05/2009 | 11:20 | Manly Vale Football Club | St Augustines Soccer Club | David Thomas 2 |
| 12 / U12/2 | 4 | 9/05/2009 | 09:50 | Harbord Seasiders United Football Club | Manly Vale Football Club | Nolans 6 |
| 12 / U12/2 | 5 | 16/05/2009 | 09:50 | Manly Vale Football Club | Beacon Hill Football Club | David Thomas 3 |
| 12 / U12/2 | 6 | 30/05/2009 | 08:20 | Collaroy Cromer Strikers Football Club | Manly Vale Football Club | St Matthews 2 |
| 12 / U12/2 | 7 | 6/06/2009 | 11:20 | Narrabeen Football Club | Manly Vale Football Club | Boondah 1 |
| 12 / U12/2 | 8 | 13/06/2009 | 09:50 | Manly Vale Football Club | Forest Killarney Football Club | David Thomas 3 |
| 12 / U12/2 | 9 | 20/06/2009 | 08:20 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 3 |
| 12 / U12/2 | 10 | 27/06/2009 | 08:20 | St Augustines Soccer Club | Manly Vale Football Club | Passmore 1 |
| 12 / U12/2 | 11 | 4/07/2009 | 09:50 | Manly Vale Football Club | Harbord Seasiders United Football Club | David Thomas 3 |
| 12 / U12/2 | 12 | 11/07/2009 | 11:20 | Beacon Hill Football Club | Manly Vale Football Club | Tristram Rd (Beacon Hill High School) |
| 12 / U12/2 | 13 | 25/07/2009 | 09:50 | Manly Vale Football Club | Collaroy Cromer Strikers Football Club | David Thomas 3 |
| 12 / U12/2 | 14 | 1/08/2009 | 09:50 | Manly Vale Football Club | Narrabeen Football Club | David Thomas 2 |
| 12 / U12/4 | 1 | 4/04/2009 | 11:20 | Manly Vale Football Club | Seaforth Football Club | David Thomas 2 |
| 12 / U12/4 | 2 | 11/04/2009 | 11:20 | Forest Killarney Football Club | Manly Vale Football Club | Melwood 2 |
| 12 / U12/4 | 3 | 2/05/2009 | 08:20 | Manly Vale Football Club | Mosman Football Club | David Thomas 3 |
| 12 / U12/4 | 4 | 9/05/2009 | 08:20 | Manly Vale Football Club | Harbord Seasiders United Football Club | Millers 3 |
| 12 / U12/4 | 5 | 16/05/2009 | 08:20 | St Augustines Soccer Club | Manly Vale Football Club | Nolans 4 |
| 12 / U12/4 | 6 | 23/05/2009 | 08:20 | Manly Vale Football Club | Wakehurst Football Club | David Thomas 3 |
| 12 / U12/4 | 7 | 30/05/2009 | 11:20 | Collaroy Cromer Strikers Football Club | Manly Vale Football Club | St Matthews 2 |
| 12 / U12/4 | 8 | 6/06/2009 | 11:20 | Manly Vale Football Club | Avalon Soccer Club | David Thomas 3 |
| 12 / U12/4 | 9 | 8/06/2009 | 09:50 | Pittwater RSL Football Club | Manly Vale Football Club | Kitchener 1 |
| 12 / U12/4 | 10 | 13/06/2009 | 09:50 | Seaforth Football Club | Manly Vale Football Club | Tania Park 2 |
| 12 / U12/4 | 11 | 20/06/2009 | 09:50 | Manly Vale Football Club | Forest Killarney Football Club | David Thomas 3 |
| 12 / U12/4 | 12 | 27/06/2009 | 08:20 | Mosman Football Club | Manly Vale Football Club | Middle Head Oval |
| 12 / U12/4 | 13 | 4/07/2009 | 11:20 | Harbord Seasiders United Football Club | Manly Vale Football Club | Nolans 4 |
| 12 / U12/4 | 14 | 11/07/2009 | 08:20 | Manly Vale Football Club | St Augustines Soccer Club | Millers 1 |
| 12 / U12/4 | 15 | 25/07/2009 | 11:20 | Wakehurst Football Club | Manly Vale Football Club | Lionel Watts 4 |
| 12 / U12/4 | 16 | 1/08/2009 | 11:20 | Manly Vale Football Club | Collaroy Cromer Strikers Football Club | David Thomas 2 |
| 12 / U12/4 | 17 | 8/08/2009 | 11:20 | Avalon Soccer Club | Manly Vale Football Club | Careel Bay 1 |
| 12 / U12/4 | 18 | 15/08/2009 | 09:50 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 3 |
| 13 / U13/3 | 1 | 4/04/2009 | 08:20 | Manly Vale Football Club | Brookvale Football Club | David Thomas 3 |
| 13 / U13/3 | 2 | 11/04/2009 | 09:50 | Collaroy Cromer Strikers Football Club | Manly Vale Football Club | David Thomas 3 |
| 13 / U13/3 | 3 | 2/05/2009 | 00:00 | Manly Vale Football Club | ~~bye~~ | |
| 13 / U13/3 | 4 | 9/05/2009 | 08:20 | Manly Vale Football Club | St Augustines Soccer Club A | David Thomas 3 |
| 13 / U13/3 | 5 | 16/05/2009 | 11:20 | Manly Vale Football Club | BTH Raiders Soccer Club | David Thomas 3 |
| 13 / U13/3 | 6 | 23/05/2009 | 08:20 | Avalon Soccer Club | Manly Vale Football Club | Careel Bay 2 |
| 13 / U13/3 | 7 | 30/05/2009 | 11:20 | Manly Vale Football Club | Forest Killarney Football Club | David Thomas 3 |
| 13 / U13/3 | 8 | 6/06/2009 | 11:20 | Wakehurst Football Club | Manly Vale Football Club | Ararat Oval |
| 13 / U13/3 | 9 | 8/06/2009 | 11:20 | Manly Vale Football Club | Pittwater RSL Football Club | Millers 2 |
| 13 / U13/3 | 10 | 13/06/2009 | 09:50 | St Augustines Soccer Club B | Manly Vale Football Club | Nolans 4 |
| 13 / U13/3 | 11 | 20/06/2009 | 11:20 | Manly Vale Football Club | Narrabeen Football Club | David Thomas 3 |
| 13 / U13/3 A | 1 | 4/07/2009 | 11:20 | Forest Killarney Football Club | Manly Vale Football Club | Rheub Hudson |
| 13 / U13/3 A | 2 | 11/07/2009 | 11:20 | Manly Vale Football Club | A St Augustines Soccer Club | David Thomas 3 |
| 13 / U13/3 A | 3 | 25/07/2009 | 11:20 | Narrabeen Football Club | Manly Vale Football Club | Jackson Road 1 |
| 13 / U13/3 A | 4 | 1/08/2009 | 8:20 | BTH Raiders Soccer Club | Manly Vale Football Club | County Road |
| 13 / U13/3 A | 5 | 8/08/2009 | 11:20 | Manly Vale Football Club | Avalon Soccer Club | David Thomas 3 |
| 14 / U14/1 | 1 | 4/04/2009 | 08:20 | Pittwater RSL Football Club | Manly Vale Football Club | Kitchener 1 |
| 14 / U14/1 | 2 | 11/04/2009 | 08:20 | Manly Vale Football Club | Seaforth Football Club | David Thomas 2 |
| 14 / U14/1 | 3 | 2/05/2009 | 08:20 | Wakehurst Football Club B | Manly Vale Football Club | Lionel Watts 3 |
| 14 / U14/1 | 4 | 9/05/2009 | 09:50 | Manly Vale Football Club | Brookvale Football Club | David Thomas 3 |
| 14 / U14/1 | 5 | 16/05/2009 | 08:20 | Mosman Football Club | Manly Vale Football Club | Middle Head Oval |
| 14 / U14/1 | 6 | 23/05/2009 | 00:00 | Manly Vale Football Club | ~~bye~~ | |
| 14 / U14/1 | 7 | 30/05/2009 | 08:20 | Manly Vale Football Club | Avalon Soccer Club | Millers 1 |
| 14 / U14/1 | 8 | 6/06/2009 | 09:50 | St Augustines Soccer Club | Manly Vale Football Club | Grahams Oval 1 |
| 14 / U14/1 | 9 | 8/06/2009 | 08:20 | Manly Vale Football Club | Wakehurst Football Club A | Millers 2 |
| 14 / U14/1 | 10 | 13/06/2009 | 08:20 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 3 |
| 14 / U14/1 | 11 | 20/06/2009 | 08:20 | Seaforth Football Club | Manly Vale Football Club | Seaforth 2 |
| 14 / U14/1 | 12 | 27/06/2009 | 08:20 | Manly Vale Football Club | Wakehurst Football Club B | David Thomas 3 |
| 14 / U14/1 | 13 | 4/07/2009 | 09:50 | Brookvale Football Club | Manly Vale Football Club | Grahams Oval 2 |
| 14 / U14/1 | 14 | 11/07/2009 | 08:20 | Manly Vale Football Club | Mosman Football Club | David Thomas 3 |
| 14 / U14/1 | 15 | 25/07/2009 | 00:00 | ~~bye~~ | Manly Vale Football Club | |
| 14 / U14/1 | 16 | 1/08/2009 | 11:20 | Avalon Soccer Club | Manly Vale Football Club | Careel Bay 2 |
| 14 / U14/1 | 17 | 8/08/2009 | 08:20 | Manly Vale Football Club | St Augustines Soccer Club | David Thomas 2 |
| 14 / U14/1 | 18 | 15/08/2009 | 09:50 | Wakehurst Football Club A | Manly Vale Football Club | Lionel Watts 3 |
| 14 / U14/3 | 1 | 4/04/2009 | 08:20 | Curl Curl Youth Club | Manly Vale Football Club | Abbott Rd 5 |
| 14 / U14/3 | 2 | 11/04/2009 | 08:20 | Manly Vale Football Club | Wakehurst Football Club | David Thomas 3 |
| 14 / U14/3 | 3 | 2/05/2009 | 09:50 | Beacon Hill Football Club | Manly Vale Football Club | David Thomas 3 |
| 14 / U14/3 | 4 | 9/05/2009 | 11:20 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 3 |
| 14 / U14/3 | 5 | 16/05/2009 | 08:20 | St Augustines Soccer Club B | Manly Vale Football Club | Millers 3 |
| 14 / U14/3 | 6 | 23/05/2009 | 08:20 | BTH Raiders Soccer Club | Manly Vale Football Club | Terrey Hills 2 |
| 14 / U14/3 | 7 | 30/05/2009 | 08:20 | St Augustines Soccer Club A | Manly Vale Football Club | Nolans 5 |
| 14 / U14/3 | 8 | 6/06/2009 | 09:50 | Seaforth Football Club | Manly Vale Football Club | Tania Park 2 |
| 14 / U14/3 | 9 | 8/06/2009 | 09:50 | Narrabeen Football Club | Manly Vale Football Club | Boondah 2 |
| 14 / U14/3 | 10 | 13/06/2009 | 08:20 | Manly Vale Football Club | Curl Curl Youth Club | Millers 1 |
| 14 / U14/3 | 11 | 20/06/2009 | 11:20 | Wakehurst Football Club | Manly Vale Football Club | Lionel Watts 2 |
| 14 / U14/3 | 12 | 27/06/2009 | 08:20 | Manly Vale Football Club | Beacon Hill Football Club | David Thomas 2 |
| 14 / U14/3 | 13 | 4/07/2009 | 08:20 | Pittwater RSL Football Club | Manly Vale Football Club | Jackson Road 2 |
| 14 / U14/3 | 14 | 11/07/2009 | 11:20 | Manly Vale Football Club | St Augustines Soccer Club B | Millers 1 |
| 14 / U14/3 | 15 | 25/07/2009 | 11:20 | Manly Vale Football Club | BTH Raiders Soccer Club | David Thomas 3 |
| 14 / U14/3 | 16 | 1/08/2009 | 08:20 | Manly Vale Football Club | St Augustines Soccer Club A | David Thomas 3 |
| 14 / U14/3 | 17 | 8/08/2009 | 09:50 | Manly Vale Football Club | Seaforth Football Club | David Thomas 2 |
| 14 / U14/3 | 18 | 15/08/2009 | 08:20 | Manly Vale Football Club | Narrabeen Football Club | Millers 1 |
| 16 / U16/2 | 1 | 4/04/2009 | 08:20 | St Augustines Soccer Club | Manly Vale Football Club | Passmore 1 |
| 16 / U16/2 | 2 | 11/04/2009 | 08:20 | Pittwater RSL Football Club | Manly Vale Football Club | Kitchener 1 |
| 16 / U16/2 | 3 | 2/05/2009 | 08:20 | Manly Vale Football Club | Wakehurst Football Club | David Thomas 2 |
| 16 / U16/2 | 4 | 9/05/2009 | 08:20 | Narrabeen Football Club | Manly Vale Football Club | Boondah 2 |
| 16 / U16/2 | 5 | 16/05/2009 | 08:20 | Manly Vale Football Club | Seaforth Football Club | David Thomas 2 |
| 16 / U16/2 | 6 | 23/05/2009 | 08:20 | BTH Raiders Soccer Club | Manly Vale Football Club | Tristram Rd (Beacon Hill High School) |
| 16 / U16/2 | 7 | 30/05/2009 | 08:20 | Manly Vale Football Club | Collaroy Cromer Strikers Football Club | David Thomas 2 |
| 16 / U16/2 | 8 | 6/06/2009 | 08:20 | Manly Vale Football Club | Curl Curl Youth Club | David Thomas 3 |
| 16 / U16/2 | 9 | 8/06/2009 | 08:20 | Avalon Soccer Club | Manly Vale Football Club | Careel Bay 2 |
| 16 / U16/2 | 10 | 13/06/2009 | 08:20 | Manly Vale Football Club | St Augustines Soccer Club | David Thomas 2 |
| 16 / U16/2 | 11 | 20/06/2009 | 08:20 | Manly Vale Football Club | Pittwater RSL Football Club | David Thomas 2 |
| 16 / U16/2 | 12 | 27/06/2009 | 08:20 | Wakehurst Football Club | Manly Vale Football Club | Lionel Watts 2 |
| 16 / U16/2 | 13 | 4/07/2009 | 08:20 | Manly Vale Football Club | Narrabeen Football Club | David Thomas 2 |
| 16 / U16/2 | 14 | 11/07/2009 | 08:20 | Seaforth Football Club | Manly Vale Football Club | Seaforth 1 |
| 16 / U16/2 | 15 | 25/07/2009 | 08:20 | Manly Vale Football Club | BTH Raiders Soccer Club | David Thomas 2 |
| 16 / U16/2 | 16 | 1/08/2009 | 08:20 | Collaroy Cromer Strikers Football Club | Manly Vale Football Club | St Matthews 3 |
| 16 / U16/2 | 17 | 8/08/2009 | 08:20 | Curl Curl Youth Club | Manly Vale Football Club | Abbott Rd 5 |
| 16 / U16/2 | 18 | 15/08/2009 | 08:20 | Manly Vale Football Club | Avalon Soccer Club | David Thomas 3 |