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 2–2double-dagger 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 2–2dagger Joe Public Manny Ramjohn Stadium
2009
Defence Force
1–0
Joe Public Marvin Lee Stadium
2010
Joe Public 1–1dagger Defence Force Marvin Lee Stadium
2011
Caledonia AIA
2–1
T&TEC Hasely Crawford Stadium
2012
Caledonia AIA
2–1
Defence Force Hasely Crawford Stadium
2013
Central FC
2–1
Defence Force Hasely Crawford Stadium