Results
All matches were played for 90 minutes duration, at the end of which if the match was still tied, penalty-kicks were used to determine the match winner.
Qualifying round
The knockout cup began in the qualifying round with Tobago United and Defence Force recording upsets over higher-seeded Ma Pau and North East Stars respectively.
| 2 September 2008 | Tobago United | 2–1 | Ma Pau | Malabar, Trinidad |
| 17:00 (UTC-4) | Hercules  68' (pen.)Hernandez 82' |
Proctor 19' |
Stadium: Larry Gomes Stadium Referee: Gordon Maloney |
| 2 September 2008 | North East Stars | 1–1 (0–3 p) | Defence Force | Malabar, Trinidad |
| 19:00 (UTC-4) | Teesdale 60' |
Jorsling 50' |
Stadium: Larry Gomes Stadium | |
| Penalties | ||||
Stewart  Cooper Jeffrey |
Pierre  Jorsling Williams |
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Quarterfinals
Fans saw a goal spree in the quarterfinals where 22 goals were scored in four matches on 12 September, which saw Jabloteh, Joe Public, Rangers, and W Connection advance to the semifinals.
| 12 September 2008 | San Juan Jabloteh | 2–0 | Tobago United | Malabar, Trinidad |
| 18:00 (UTC-4) | Noel 14' (pen.) Forbes 87' |
Stadium: Larry Gomes Stadium |
| 12 September 2008 | United Petrotrin | 2–4 | Joe Public | Marabella, Trinidad |
| 18:00 (UTC-4) | Aguillera 11' Woodley 18' |
Richardson 5', 19', 26' Calderon 44' |
Stadium: Manny Ramjohn Stadium Referee: Phillip Jordan |
| 12 September 2008 | St. Ann's Rangers | 3–3 (4–3 p) | Caledonia AIA | Malabar, Trinidad |
| 20:00 (UTC-4) | Thomas 37' Edwards 41'Belgrave 53' (pen.) |
Moore 6' Smith 18', 26' |
Stadium: Larry Gomes Stadium |
| 12 September 2008 | W Connection | 5–2 | Defence Force | Marabella, Trinidad |
| 20:00 (UTC-4) | Hector 15', 53' Faña 40'Viana 43'Toussaint 89' |
Williams 6' Carter 57' |
Stadium: Manny Ramjohn Stadium |
Semifinals
On 19 September 2008, Joe Public used a lone goal from Gregory Richardson to advance to the final. In the other semifinal, W Connection blanked St. Ann's Rangers after goals from Jonathan Faña and Atiba McKnight on either side of half-time.
| 19 September 2008 | San Juan Jabloteh | 0–1 | Joe Public | Marabella, Trinidad |
| 20:00 (UTC-4) | Report | Richardson 48' |
Stadium: Manny Ramjohn Stadium Referee: Austin Perelion |
| 19 September 2008 | W Connection | 2–0 | St. Ann's Rangers | Marabella, Trinidad |
| 18:00 (UTC-4) | Faña 8' McKnight 74' |
Report | Stadium: Manny Ramjohn Stadium |
Third place
With wins by Joe Public and W Connection in the semifinals; San Juan Jabloteh and St. Ann's Rangers were sent to the third place match. Before the final match, St. Ann's Rangers used strikes from Keyon Edwards and Josimar Belgrave in two minutes to put away top seeded San Juan Jabloteh for a third-place finish.
| 26 September 2008 | San Juan Jabloteh | 1–2 | St. Ann's Rangers | Marabella, Trinidad |
| 18:00 (UTC-4) | Marcano 67' |
Report | Edwards 60' Belgrave 61' |
Stadium: Manny Ramjohn Stadium Referee: Julien Drayton |
Final
W Connection claimed their fifth consecutive title and sixth overall in the tournament's nine-year history with a win over Joe Public in the final. The match was held on 26 September in Manny Ramjohn Stadium. After being dead-locked 2–2 at the end of regulation, W Connection used a miss by Joe Public's Jason Springer on the twelfth kick from the penalty spot to win 6–5 in the shootout.[2] Although Joe Public finished runners-up, Gregory Richardson led the tournament with four goals scored.
| 26 September 2008 | W Connection | 2–2 (6–5 p) | Joe Public | Marabella, Trinidad |
| 20:00 (UTC-4) | Toussaint 18' Faña 35' |
Report | Harvey 11' Thomas 55' |
Stadium: Manny Ramjohn Stadium Referee: Gregory Hospedales |
| Penalties | ||||
| Faña Toussaint Seabra Viveros Joseph Cupid McKnight |
Baptiste Dwarika Harvey Saunders Wolfe Thomas Springer |
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