| Date | Home | Score | Away |
| Round 1 | |||
| 9/21/2008 | Boys Town | 1 - 0 | Arnett Gardens |
| 9/21/2008 | Harbour View FC | 4 - 0 | Village United |
| 9/21/2008 | Portmore United | 2 - 0 | Rivoli United |
| 9/21/2008 | Sporting Centra | 2 - 1 | Reno FC |
| 9/21/2008 | Tivoli Gardens | 1 - 1 | Meadhaven Unite |
| 39712 | Waterhouse FC | 1 - 1 | St. Georges |
| Round 2 | |||
| 9/24/2008 | Arnett Gardens | 0 - 1 | Portmore United |
| 9/24/2008 | Meadhaven Unite | 2 - 2 | Sporting Centra |
| 9/24/2008 | Reno FC | 0 - 0 | Tivoli Gardens |
| 9/24/2008 | Rivoli United | 0 - 1 | Waterhouse FC |
| 9/24/2008 | St. Georges | 0 - 0 | Harbour View FC |
| 39715 | Village United | 1 - 1 | Boys Town |
| Round 3 | |||
| 9/28/2008 | Arnett Gardens | 0 - 1 | Waterhouse FC |
| 9/28/2008 | Meadhaven Unite | 1 - 2 | Harbour View FC |
| 9/28/2008 | Reno FC | p - p | Boys Town |
| 9/28/2008 | Rivoli United | 1 - 0 | Sporting Centra |
| 9/28/2008 | St. Georges | 0 - 0 | Tivoli Gardens |
| 39719 | Village United | 1 - 1 | Portmore United |
| Round 4 | |||
| 10/5/2008 | Boys Town | - | St. Georges |
| 10/5/2008 | Harbour View FC | - | Rivoli United |
| 10/5/2008 | Portmore United | - | Reno FC |
| 10/5/2008 | Sporting Centra | - | Arnett Gardens |
| 10/5/2008 | Tivoli Gardens | - | Village United |
| 10/5/2008 | Waterhouse FC | - | Meadhaven Unite |
| Round 5 | |||
| 10/19/2008 | Arnett Gardens | - | Tivoli Gardens |
| 10/19/2008 | Meadhaven Unite | - | Portmore United |
| 10/19/2008 | Reno FC | - | Harbour View FC |
| 10/19/2008 | Rivoli United | - | Boys Town |
| 10/19/2008 | St. Georges | - | Sporting Centra |
| 10/19/2008 | Village United | - | Waterhouse FC |
| Round 6 | |||
| 10/22/2008 | Boys Town | - | Meadhaven Unite |
| 10/22/2008 | Harbour View FC | - | Arnett Gardens |
| 10/22/2008 | Portmore United | - | St. Georges |
| 10/22/2008 | Sporting Centra | - | Village United |
| 10/22/2008 | Tivoli Gardens | - | Rivoli United |
| 10/22/2008 | Waterhouse FC | - | Reno FC |
| Round 7 | |||
| 10/26/2008 | Arnett Gardens | - | Reno FC |
| 10/26/2008 | Boys Town | - | Harbour View FC |
| 10/26/2008 | Portmore United | - | Sporting Centra |
| 10/26/2008 | St. Georges | - | Meadhaven Unite |
| 10/26/2008 | Tivoli Gardens | - | Waterhouse FC |
| 10/26/2008 | Village United | - | Rivoli United |
| Round 8 | |||
| 11/2/2008 | Harbour View FC | - | Tivoli Gardens |
| 11/2/2008 | Meadhaven Unite | - | Arnett Gardens |
| 11/2/2008 | Reno FC | - | Village United |
| 11/2/2008 | Rivoli United | - | St. Georges |
| 11/2/2008 | Sporting Centra | - | Boys Town |
| 11/2/2008 | Waterhouse FC | - | Portmore United |
| Round 9 | |||
| 11/9/2008 | Boys Town | - | Waterhouse FC |
| 11/9/2008 | Harbour View FC | - | Sporting Centra |
| 11/9/2008 | Reno FC | - | Rivoli United |
| 11/9/2008 | St. Georges | - | Arnett Gardens |
| 11/9/2008 | Tivoli Gardens | - | Portmore United |
| 11/9/2008 | Village United | - | Meadhaven Unite |
| Round 10 | |||
| 11/12/2008 | Arnett Gardens | - | Village United |
| 11/12/2008 | Meadhaven Unite | - | Rivoli United |
| 11/12/2008 | Portmore United | - | Boys Town |
| 11/12/2008 | Sporting Centra | - | Tivoli Gardens |
| 11/12/2008 | St. Georges | - | Reno FC |
| 11/12/2008 | Waterhouse FC | - | Harbour View FC |
| Round 11 | |||
| 11/16/2008 | Boys Town | - | Tivoli Gardens |
| 11/16/2008 | Meadhaven Unite | - | Reno FC |
| 11/16/2008 | Portmore United | - | Harbour View FC |
| 11/16/2008 | Rivoli United | - | Arnett Gardens |
| 11/16/2008 | Sporting Centra | - | Waterhouse FC |
| 11/16/2008 | Village United | - | St. Georges |
| Round 12 | |||
| 11/30/2008 | Arnett Gardens | - | Boys Town |
| 11/30/2008 | Meadhaven Unite | - | Tivoli Gardens |
| 11/30/2008 | Reno FC | - | Sporting Centra |
| 11/30/2008 | Rivoli United | - | Portmore United |
| 11/30/2008 | St. Georges | - | Waterhouse FC |
| 11/30/2008 | Village United | - | Harbour View FC |
| Round 13 | |||
| 12/17/2008 | Boys Town | - | Village United |
| 12/17/2008 | Harbour View FC | - | St. Georges |
| 12/17/2008 | Portmore United | - | Arnett Gardens |
| 12/17/2008 | Sporting Centra | - | Meadhaven Unite |
| 12/17/2008 | Tivoli Gardens | - | Reno FC |
| 12/17/2008 | Waterhouse FC | - | Rivoli United |
| Round 14 | |||
| 12/21/2008 | Boys Town | - | Reno FC |
| 12/21/2008 | Harbour View FC | - | Meadhaven Unite |
| 12/21/2008 | Portmore United | - | Village United |
| 12/21/2008 | Sporting Centra | - | Rivoli United |
| 12/21/2008 | Tivoli Gardens | - | St. Georges |
| 12/21/2008 | Waterhouse FC | - | Arnett Gardens |
| Round 15 | |||
| 12/28/2008 | Arnett Gardens | - | Sporting Centra |
| 12/28/2008 | Meadhaven Unite | - | Waterhouse FC |
| 12/28/2008 | Reno FC | - | Portmore United |
| 12/28/2008 | Rivoli United | - | Harbour View FC |
| 12/28/2008 | St. Georges | - | Boys Town |
| 12/28/2008 | Village United | - | Tivoli Gardens |
| Round 16 | |||
| 1/4/2009 | Boys Town | - | Rivoli United |
| 1/4/2009 | Harbour View FC | - | Reno FC |
| 1/4/2009 | Portmore United | - | Meadhaven Unite |
| 1/4/2009 | Sporting Centra | - | St. Georges |
| 1/4/2009 | Tivoli Gardens | - | Arnett Gardens |
| 1/4/2009 | Waterhouse FC | - | Village United |
| Round 17 | |||
| 1/7/2009 | Arnett Gardens | - | Harbour View FC |
| 1/7/2009 | Meadhaven Unite | - | Boys Town |
| 1/7/2009 | Reno FC | - | Waterhouse FC |
| 1/7/2009 | Rivoli United | - | Tivoli Gardens |
| 1/7/2009 | St. Georges | - | Portmore United |
| 1/7/2009 | Village United | - | Sporting Centra |
| Round 18 | |||
| 1/11/2009 | Harbour View FC | - | Boys Town |
| 1/11/2009 | Meadhaven Unite | - | St. Georges |
| 1/11/2009 | Reno FC | - | Arnett Gardens |
| 1/11/2009 | Rivoli United | - | Village United |
| 1/11/2009 | Sporting Centra | - | Portmore United |
| 1/11/2009 | Waterhouse FC | - | Tivoli Gardens |
| Round 19 | |||
| 1/18/2009 | Arnett Gardens | - | Meadhaven Unite |
| 1/18/2009 | Boys Town | - | Sporting Centra |
| 1/18/2009 | Portmore United | - | Waterhouse FC |
| 1/18/2009 | St. Georges | - | Rivoli United |
| 1/18/2009 | Tivoli Gardens | - | Harbour View FC |
| 1/18/2009 | Village United | - | Reno FC |
| Round 20 | |||
| 1/25/2009 | Arnett Gardens | - | St. Georges |
| 1/25/2009 | Meadhaven Unite | - | Village United |
| 1/25/2009 | Portmore United | - | Tivoli Gardens |
| 1/25/2009 | Rivoli United | - | Reno FC |
| 1/25/2009 | Sporting Centra | - | Harbour View FC |
| 1/25/2009 | Waterhouse FC | - | Boys Town |
| Round 21 | |||
| 1/28/2009 | Boys Town | - | Portmore United |
| 1/28/2009 | Harbour View FC | - | Waterhouse FC |
| 1/28/2009 | Reno FC | - | St. Georges |
| 1/28/2009 | Rivoli United | - | Meadhaven Unite |
| 1/28/2009 | Tivoli Gardens | - | Sporting Centra |
| 1/28/2009 | Village United | - | Arnett Gardens |
| Round 22 | |||
| 2/8/2009 | Arnett Gardens | - | Rivoli United |
| 2/8/2009 | Harbour View FC | - | Portmore United |
| 2/8/2009 | Reno FC | - | Meadhaven Unite |
| 2/8/2009 | St. Georges | - | Village United |
| 2/8/2009 | Tivoli Gardens | - | Boys Town |
| 2/8/2009 | Waterhouse FC | - | Sporting Centra |
| Round 23 | |||
| 2/22/2009 | Boys Town | - | Arnett Gardens |
| 2/22/2009 | Harbour View FC | - | Village United |
| 2/22/2009 | Portmore United | - | Rivoli United |
| 2/22/2009 | Sporting Centra | - | Reno FC |
| 2/22/2009 | Tivoli Gardens | - | Meadhaven Unite |
| 2/22/2009 | Waterhouse FC | - | St. Georges |
| Round 24 | |||
| 3/1/2009 | Arnett Gardens | - | Portmore United |
| 3/1/2009 | Meadhaven Unite | - | Sporting Centra |
| 3/1/2009 | Reno FC | - | Tivoli Gardens |
| 3/1/2009 | Rivoli United | - | Waterhouse FC |
| 3/1/2009 | St. Georges | - | Harbour View FC |
| 3/1/2009 | Village United | - | Boys Town |
| Round 25 | |||
| 3/4/2009 | Arnett Gardens | - | Waterhouse FC |
| 3/4/2009 | Meadhaven Unite | - | Harbour View FC |
| 3/4/2009 | Reno FC | - | Boys Town |
| 3/4/2009 | Rivoli United | - | Sporting Centra |
| 3/4/2009 | St. Georges | - | Tivoli Gardens |
| 3/4/2009 | Village United | - | Portmore United |
| Round 26 | |||
| 3/8/2009 | Boys Town | - | St. Georges |
| 3/8/2009 | Harbour View FC | - | Rivoli United |
| 3/8/2009 | Portmore United | - | Reno FC |
| 3/8/2009 | Sporting Centra | - | Arnett Gardens |
| 3/8/2009 | Tivoli Gardens | - | Village United |
| 3/8/2009 | Waterhouse FC | - | Meadhaven Unite |
| Round 27 | |||
| 3/15/2009 | Arnett Gardens | - | Tivoli Gardens |
| 3/15/2009 | Meadhaven Unite | - | Portmore United |
| 3/15/2009 | Reno FC | - | Harbour View FC |
| 3/15/2009 | Rivoli United | - | Boys Town |
| 3/15/2009 | St. Georges | - | Sporting Centra |
| 3/15/2009 | Village United | - | Waterhouse FC |
| Round 28 | |||
| 3/18/2009 | Boys Town | - | Meadhaven Unite |
| 3/18/2009 | Harbour View FC | - | Arnett Gardens |
| 3/18/2009 | Portmore United | - | St. Georges |
| 3/18/2009 | Sporting Centra | - | Village United |
| 3/18/2009 | Tivoli Gardens | - | Rivoli United |
| 3/18/2009 | Waterhouse FC | - | Reno FC |
| Round 29 | |||
| 3/22/2009 | Arnett Gardens | - | Reno FC |
| 3/22/2009 | Boys Town | - | Harbour View FC |
| 3/22/2009 | Portmore United | - | Sporting Centra |
| 3/22/2009 | St. Georges | - | Meadhaven Unite |
| 3/22/2009 | Tivoli Gardens | - | Waterhouse FC |
| 3/22/2009 | Village United | - | Rivoli United |
| Round 30 | |||
| 4/5/2009 | Harbour View FC | - | Tivoli Gardens |
| 4/5/2009 | Meadhaven Unite | - | Arnett Gardens |
| 4/5/2009 | Reno FC | - | Village United |
| 4/5/2009 | Rivoli United | - | St. Georges |
| 4/5/2009 | Sporting Centra | - | Boys Town |
| 4/5/2009 | Waterhouse FC | - | Portmore United |
| Round 31 | |||
| 4/12/2009 | Boys Town | - | Waterhouse FC |
| 4/12/2009 | Harbour View FC | - | Sporting Centra |
| 4/12/2009 | Reno FC | - | Rivoli United |
| 4/12/2009 | St. Georges | - | Arnett Gardens |
| 4/12/2009 | Tivoli Gardens | - | Portmore United |
| 4/12/2009 | Village United | - | Meadhaven Unite |
| Round 32 | |||
| 4/19/2009 | Arnett Gardens | - | Village United |
| 4/19/2009 | Meadhaven Unite | - | Rivoli United |
| 4/19/2009 | Portmore United | - | Boys Town |
| 4/19/2009 | Sporting Centra | - | Tivoli Gardens |
| 4/19/2009 | St. Georges | - | Reno FC |
| 4/19/2009 | Waterhouse FC | - | Harbour View FC |
| Round 33 | |||
| 4/26/2009 | Boys Town | - | Tivoli Gardens |
| 4/26/2009 | Meadhaven Unite | - | Reno FC |
| 4/26/2009 | Portmore United | - | Harbour View FC |
| 4/26/2009 | Rivoli United | - | Arnett Gardens |
| 4/26/2009 | Village United | - | St. Georges |
| 4/26/2009 | Waterhouse FC | - | Sporting Centra |