| Rank | Team | Played | W | D | L | Goals | Diff. | Points | |||
| 1 |
![]() | (2) |
|
W Connection FC | 27 | 19 | 4 | 4 | 53:18 | 35 | 61 |
| 2 |
![]() | (1) |
|
San Juan Jabloteh | 27 | 19 | 4 | 4 | 55:23 | 32 | 61 |
| 3 |
![]() | (4) |
|
Caledonia AIA | 27 | 12 | 5 | 10 | 42:38 | 4 | 41 |
| 4 |
![]() | (5) |
|
Joe Public | 27 | 12 | 4 | 11 | 47:36 | 11 | 40 |
| 5 |
![]() | (7) |
|
North East Stars | 27 | 12 | 4 | 11 | 36:34 | 2 | 40 |
| 6 |
![]() | (6) |
|
United Petrotrin | 27 | 10 | 7 | 10 | 34:42 | -8 | 37 |
| 7 |
![]() | (3) |
|
St. Ann's Rangers | 27 | 9 | 7 | 11 | 50:52 | -2 | 34 |
| 8 |
![]() | (8) |
|
Defence Force | 27 | 7 | 7 | 13 | 41:47 | -6 | 28 |
| 9 |
![]() | (9) |
|
Ma Pau SC | 27 | 7 | 4 | 16 | 33:63 | -30 | 25 |
| 10 |
![]() | (10) |
|
Tobago United | 27 | 3 | 4 | 20 | 25:63 | -38 | 13 |
| Tuesday, 23 September 2008 | ||||||||||||
| PSRG | 05:00PM | ![]() | United Petrotrin | - | ![]() | Defence Force | 0 | : | 0 | |||
|
MRS | 05:00PM | ![]() | Ma Pau SC | - | ![]() | North East Stars | 1 | : | 4 | ||
|
LGS | 05:00PM | ![]() | Caledonia AIA | - | ![]() | San Juan Jabloteh | 1 | : | 3 | ||
| Monday, 29 September 2008 | ||||||||||||
|
|
05:00PM | ![]() | St. Ann's Rangers | - | ![]() | Tobago United | 2 | : | 1 | ||
| Thursday, 20 November 2008 | ||||||||||||
|
ABS | 05:00PM | ![]() | W Connection FC | - | ![]() | Joe Public | 2 | : | 0 | ||
| Saturday, 04 October 2008 | ||||||||||||
|
ABS | 05:00PM | ![]() | W Connection FC | - | ![]() | North East Stars | 1 | : | 0 | ||
|
PSRG | 05:00PM | ![]() | United Petrotrin | - | ![]() | Tobago United | 2 | : | 1 | ||
|
MRS | 05:00PM | ![]() | Ma Pau SC | - | ![]() | Caledonia AIA | 2 | : | 1 | ||
| Tuesday, 07 October 2008 | ||||||||||||
|
|
05:00PM | ![]() | Defence Force | - | ![]() | San Juan Jabloteh | 2 | : | 4 | ||
| Thursday, 06 November 2008 | ||||||||||||
|
MLS | 04:00PM | ![]() | Joe Public | - | ![]() | St. Ann's Rangers | 6 | : | 0 | ||
| Tue, September 16, 2008 | |||||
| WC | - | MAP | 2 | : | 1 |
| SAR | - | DF | 1 | : | 5 |
| SJJ | - | NES | 2 | : | 0 |
| Sun, September 21, 2008 | |||||
| CAL | - | UP | 3 | : | 1 |
| Mon, October 13, 2008 | |||||
| JP | - | TBU | 2 | : | 1 |
| Extended view |
| Devon Jorsling (DF) | 21 | |
| Kerry Baptiste (JP) | 17 | |
| Josimar Belgrave (SAR) | 15 | |
| Roen Nelson (JP) | 14 | |
| Collie Hercules (TBU) | 11 |
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