Trinidad and Tobago League Cup Finals Results

| Season | Winner | Score | Runners_up | Venue_ |
|---|---|---|---|---|
| 2000 | San Juan Jabloteh | 1–0 | Defence Force | Marvin Lee Stadium |
| 2001 | W Connection | 1–0 | Caledonia AIA | Manny Ramjohn Stadium |
| 2002 | Defence Force | 2–0 | W Connection | Hasely Crawford Stadium |
| 2003 | San Juan Jabloteh | * 1–1* | W Connection | Manny Ramjohn Stadium |
| 2004 | W Connection | ‡ 2–2 | Defence Force | Manny Ramjohn Stadium |
| 2005 | W Connection | 3–1 | San Juan Jabloteh | Manny Ramjohn Stadium |
| 2006 | W Connection | 3–1 | North East Stars | Manny Ramjohn Stadium |
| 2007 | W Connection | 2–0 | Caledonia AIA | Manny Ramjohn Stadium |
| 2008 | W Connection | † 2–2 | Joe Public | Manny Ramjohn Stadium |
| 2009 | Defence Force | 1–0 | Joe Public | Marvin Lee Stadium |