Campeões
| Key |
| * |
Partido decidido na prorrogação |
| † |
Partido decidido por pênaltis depois do tempo regulamentar |
| ‡ |
Partido decidido por pênaltis depois da porrogação |
| Bold |
Equipe campeão também da Liga |
| Italics |
Equipe que na pertencia a divisão de elite |
| Temporada |
Campeão |
Resultado |
Vice-Campeão |
Estádio |
|---|
| 1927 |
Shamrock |
4–2 |
Leaseholds |
|
| 1928 |
Southern Casuals |
|
|
|
| 1929 |
Everton |
3–2 |
Maple Club |
|
| 1930 |
Everton |
|
|
|
| 1931 |
Everton |
|
|
|
| 1932 |
Everton |
|
|
|
| 1933 |
Season not contested |
| 1934 |
Casuals |
|
|
|
| 1935 |
Sporting Club |
|
|
|
| 1936 |
Shamrock |
|
|
|
| 1937 |
United British Oilfields Trinidad |
3–2 |
Shamrock |
|
| 1938 |
West Ham |
2–0 |
San Fernando |
|
| 1939 |
Casuals |
|
|
|
| 1940 |
Maple Club |
|
|
|
| 1941 |
United British Oilfields Trinidad |
|
|
|
| (R) 1942 (R) |
Spitfire |
3–2 |
Colts |
|
| (R) 1943 (R) |
United British Oilfields Trinidad |
3–1 |
Sporting Club |
|
| 1944 |
Colts |
1–0 |
Sheffield |
|
| 1945 |
Colts |
5–0 |
Forest Reserve |
|
| 1946 |
Maple Club |
|
|
|
| 1947 |
Notre Dame |
2–1 |
United British Oilfields Trinidad |
|
| 1948 |
Colts |
|
|
|
| 1949 |
Maple Club |
|
Carlton |
|
| 1950 |
United British Oilfields Trinidad |
3–1 |
Hurricanes |
|
| 1951 |
United British Oilfields Trinidad |
* 1–1 * |
Providence |
|
| 1952 |
Malvern United |
2–1 |
United British Oilfields Trinidad |
|
| 1953 |
Maple Club |
1–0 |
Juniors |
|
| 1954 |
United British Oilfields Trinidad |
4–0 |
Providence |
|
| 1955 |
Malvern United |
1–0 |
United British Oilfields Trinidad |
|
| 1956 |
Trinidad Petroleum Development |
2–0 |
Notre Dame |
|
| 1957 |
Shamrock |
* 2–2 * |
Shell |
|
| 1958 |
Casuals |
1–0 |
Trinidad Petroleum Development |
|
| 1959 |
Shamrock |
1–0 |
BP Fyzabad |
|
| 1960 |
Malvern United |
2–0 |
Trinidad Petroleum Development |
|
| 1961 |
Malvern United |
* 1–1 * |
BP Fyzabad |
|
| 1962 |
Dynamos |
1–0 |
BP Fyzabad |
|
| 1963 |
Maple Club |
3–0 |
Malvern United |
|
| 1964 |
Paragon |
1–0 |
BP Palo Seco |
|
| 1965 |
Malvern United |
|
BP Palo Seco |
|
| 1966 |
Juniors |
|
Regiment |
|
| 1967 |
Regiment |
4–3 |
Juniors |
|
| 1968 |
Malvern United |
|
|
|
| 1969 |
Point Fortin |
4–2 |
Harvard |
|
| 1970 |
Maple Club |
3–0 |
Texaco |
|
| 1971 |
Season not contested |
| 1972 |
Maple Club |
3–0 |
Texaco |
|
| 1973 |
Season not contested |
| 1974 |
Defence Force |
|
|
|
| 1975 |
Police FC |
|
|
|
| 1976 |
Falcons F.C. |
|
|
|
| 1977 |
Malvern United |
2–1 |
Caroni |
|
| 1978 |
Falcons |
|
|
|
| 1979–1980 |
Season not contested |
| 1981 |
Defence Force |
5–0 |
Memphis |
|
| 1982 |
ASL Sports Club |
|
|
|
| 1983 |
ASL Sports Club |
|
|
|
| 1984 |
Motown United |
|
|
|
| 1985 |
Defence Force |
‡ 1–1 ‡ |
Trintoc |
|
| 1986 |
Trintoc |
|
|
|
| 1987 |
La Brea Angels |
|
|
|
| 1988 |
Trintoc |
|
|
|
| 1989 |
Defence Force |
|
|
|
| 1990 |
Police FC |
‡ ‡ |
Superstar Rangers |
|
| 1991 |
Defence Force |
|
|
|
| 1992 |
Motown United |
|
|
|
| 1993 |
Trintoc |
|
|
|
| (R) 1994 (R) |
Police FC |
‡ 1–1 ‡ |
Superstar Rangers |
|
| 1995 |
United Petrotrin |
|
Defence Force |
|
| 1996 |
Defence Force |
|
Police FC |
|
| 1997 |
United Petrotrin |
3–1 |
Superstar Rangers |
Queen's Park Oval |
| 1998 |
San Juan Jabloteh |
* 3–2 * |
Defence Force |
|
| 1999 |
W Connection |
* 2–1 * |
Joe Public |
Marvin Lee Stadium |
| 2000 |
W Connection |
† 1–1 ‡ |
Joe Public |
Gilbert Park |
| 2001 |
Joe Public |
1–0 |
Carib |
Marvin Lee Stadium |
| 2002 |
W Connection |
5–1 |
Arima Fire |
Marvin Lee Stadium |
| 2003 |
North East Stars |
‡ 2–2 ‡ |
W Connection |
Marvin Lee Stadium |
| 2004 |
Season not finished |
| 2005 |
San Juan Jabloteh |
2–1 |
Defence Force |
Marvin Lee Stadium |
| 2006 |
WASA |
‡ 3–3 ‡ |
North East Stars |
Estadio Ato Boldon |
| 2007 |
Joe Public |
1–0 |
Caledonia AIA |
Marvin Lee Stadium |
| 2008 |
Caledonia AIA |
3–2 |
W Connection |
Marvin Lee Stadium |
| 2009 |
Joe Public |
* 3–2 * |
W Connection |
Marvin Lee Stadium |
| 2010–11 |
San Juan Jabloteh |
1–0 |
North East Stars |
Marvin Lee Stadium |
| 2011–12 |
Caledonia AIA |
1–0 |
Defence Force |
Manny Ramjohn Stadium |
| 2012–13 |
Caledonia AIA |
2–0 |
Central FC |
Estadio Ato Boldon |
| 2013–14 |
W Connection |
‡ 2–2 ‡ |
Central FC |
Estadio Ato Boldon |
| 2014-15
|
North East Stars |
0-0‡ |
W Connection |
|
| 2015-16 |
Não Disputado |
|
|
|
| 2016-17 |
W Connection |
3-1 |
Police FC |
|