Trinidad and Tobago - List of Cup Winners


FA Cup

The FA Cup was presented by the (English) Football Association in 1906 and used for various competitions until a regular FA Cup Trophy tournament was started in 1927.

1927    Shamrock               4-2 Leaseholds
1928    Southern Casuals
1929    Everton                abd Maple Club              [Maple walked off at 3-2 to Everton]
1930    Everton
1931    Everton
1932    Everton  
1933      not contested
1934    Casuals
1935    Sporting Club
1936    Shamrock               3-2 UBOT       
1937    UBOT                   3-2 Shamrock 
1938    West Ham               2-0 San Fernando
1939    Casuals
1940    Maple Club
1941    UBOT
1942    Spitfire           1-1 3-2 Colts
1943    UBOT               1-1 3-1 Sporting Club
1944    Colts                  1-0 Sheffield
1945    Colts                  5-0 Forest Reserve
1946    Maple Club
1947    Notre Dame             2-1 UBOT
1948    Colts
1949    Maple Club and Carlton (shared)
1950    UBOT                   3-1 Hurricanes
1951    UBOT and Providence (shared after 1-1 draw)
1952    Malvern                2-1 UBOT
1953    Maple Club             1-0 Juniors
1954    UBOT                   4-0 Providence
1955    Malvern                1-0 UBOT (aka UBAA)
1956    TPD                    2-0 Notre Dame
1957    Shell and Shamrock (shared after 2-2 draw after extra time)
1958    Casuals                1-0 Trinidad Petroleum Development     
1959    Shamrock               1-0 Apex
1960    Malvern                2-0 Trinidad Petroleum Development 
1961    Malvern and Apex (aka BP Fyzabad) (shared after 1-1 draw)
1962    Dynamos                1-0 Apex
1963    Maple Club             3-0 Malvern
1964    Paragon                1-0 BP Palo Seco
1965    Malvern and BP Palo Seco (shared)
1966    Regiment and Juniors (shared)
1967    Regiment               4-3 Juniors
1968    Malvern
1969    Point Fortin           4-2 Harvard
1970    Maple Club             3-0 Texaco
1971      not held
1972    Maple Club             3-0 Forest Reserve
1973      not held
1974    Defence Force
1975    Police FC
1976    Falcons
1977    Malvern                2-1 Caroni
1978    Falcons
1979/80   not held
1981    Defence Force          5-0 Memphis
1982    ASL Sports Club
1983    ASL Sports Club
1984    Motown United
1985    Defence Force          1-1 Trintoc                 [Defence Force on pen] 
1986    Trintoc
1987    La Brea Angels
1988    Trintoc
1989    Defence Force
1990    Police FC              drw Superstar Rangers       [Police on pen]
1991    Defence Force
1992    Motown
1993    Trintoc
1994    Police FC          0-0 1-1 Superstar Rangers       [3-0 pen]
1995    United Petrotrin       bt  Defence Force
1996    Defence Force          bt  Police FC
1997    United Petrotrin       3-1 Superstar Rangers
1998    CLF San Juan Jabloteh  3-2 Defence Force
1999    Williams Connection    2-1 Joe Public        
2000    Williams Connection    1-1 Joe Public              [5-4 pen] 
2001    Joe Public             1-0 Carib FC
2002    Williams Connection    5-1 Arima Fire
2003    North East Stars       2-2 Williams Connection     [aet, 4-1 pen]
2004      not finished
2005    San Juan Jabloteh      2-1 Defence Force
2006    WASA                   2-2 North East Stars        [aet, 4-2 pen]
2007    Joe Public             1-0 Caledonia AIA
2008    Caledonia AIA          3-2 Williams Connection
2009    Joe Public             3-2 Williams Connection     [aet]
2010/11 San Juan Jabloteh      1-0 North East Stars  
2011/12 Caledonia AIA          1-0 Defence Force
2012/13 Caledonia AIA          2-0 Central FC    
2013/14 Williams Connection    2-2 Central FC              [aet, 6-5 pen]
2014/15 North East Stars       0-0 Williams Connection     [aet, 5-4 pen]
2015/16   not played
2017    Williams Connection    3-1 Police FC     

NB: from 1927 to 1937 Leaseholds played and lost 5 finals (2 each against
    Everton and Sporting Club)

The 2000 edition reportedly was the 72nd (69th according to winners list above)

Number of Titles (89; 6 cups were shared)

 7 Maple               (1 shared)
   Malvern             (2 shared)

 6 Defence Force       
   UBOT                (1 shared)  [United British Oilfields Trinidad]

 5 Williams Connection 

 4 Everton             
   Shamrock            (1 shared)

 3 Caledonia AIA       
   Casuals             
   Colts               
   Joe Public          
   Police              
   San Juan Jabloteh   
   Trintoc              

 2 ASL Sports Club                 [Aviation Services Limited]
   Falcons              
   Motown United        
   North East Stars    
   United Petrotrin    
   Regiment            (1 shared)

 1 Dynamos             
   La Brea Angels      
   Notre Dame          
   Paragon             
   Point Fortin        
   Southern Casuals    
   Spitfire            
   Sporting Club       
   TPD                             [Trinidad Petroleum Development] 
   WASA                
   West Ham            
   Apex                (shared)    [also known as BP Fyzabad]
   BP Palo Seco        (shared)
   Carlton             (shared)
   Juniors             (shared)
   Providence          (shared)
   Shell               (shared)


Number of League-and-Cup Doubles (23)

 5 Defence Force             [1974, 1981, 1985, 1989, 1996]

 3 Everton                   [1930, 1931, 1932]

 2 ASL Sports Club           [1982, 1983]
 2 Maple                     [1953, 1963]
 2 Trintoc                   [1986, 1988]
 2 Williams Connection       [2000, 2014]

 1 Casuals                   [1934]
 1 Colts                     [1945]
 1 Joe Public                [2009]
 1 Paragon                   [1964]
 1 Police                    [1994]
 1 Regiment                  [1966]   [cup shared]
 1 Shamrock                  [1959]


BDV Cup

NB: BDV = Best Dark Virginia; apparently a type of league cup restricted
    to first division clubs, though Malvern won it in 1946 while at the 
    second division (from which they promoted that year);
    called SBDV Cup between 1933 and 1942;
    the 1910 edition was the first, the 1974 edition was the last

1910    Casuals          
1911    Casuals                3-2 Shamrock
1912    Southern               3-0 Casuals 
1913    Southern               2-1 Casuals      
1914    Southern               bt  Shamrock
1915    Southern               1-0 Clydesdale
1916      not held
1917    Queen's Park CC
1918    Queen's Park CC
1919    Queen's Park CC
1920    Casuals                2-1 Shamrock
1921    Maple                  bt  Shannon
1922    St. Mary's             2-0 Casuals
1923    St. Mary's
1924    Casuals
1925    Sporting Club
1926    Casuals
1927      not held
1928    Everton                3-1 Maple
1929    Casuals
1930      not held
1931      not held  
1932      not held
1933    Shamrock
1934    Casuals
1935    Constabulary
1936    Shamrock
1937    Shamrock
1938    Shamrock               3-1 Colts
1939    Shamrock
1940    Colts                  3-0 Police
1941    Notre Dame
1942    Colts
1943    First Batallion        3-0 Colts
1944    Bradford
1945    Shamrock
1946    Malvern                6-2 Sporting Club
1947    Malvern
1948    Shamrock
1949    Malvern                3-1 Colts
1950      not held
1951    Colts
1952    Maple
1953    Maple                 
1954    Colts                  1-0 Malvern
1955    Colts                  2-0 Juniors
1956    Maple                  1-0 Shamrock
1957    Maple                  2-1 Malvern
1958    Providence
1959    Shamrock               2-1 Malvern 
1960    Malvern                2-0 Sporting Club  
1961    Dynamos SC
1962    Malvern                1-0 Maple
1963    Colts
1964    Maple                  bt  Colts
1965    Maple                  4-1 Paragon
1966      not held      
1967    Regiment
1968    Paragon                2-1 Malvern
1969    Malvern 
1970    Regiment
1971      not held
1972    Colts                  1-0 Malvern 
1973    Malvern                1-0 Essex
1974    Boissierre Youth       

Number of Wins (57)
      
 8 Shamrock  

 7 Casuals
   Colts
   Malvern
   Maple

 4 Southern 

 3 Queen's Park CC

 2 Regiment
   St. Mary's

 1 Boissierre Youth   
   Bradford
   Constabulary
   Dynamos SC
   Everton
   First Batallion
   Notre Dame
   Paragon
   Providence
   Sporting Club

Bonanza Cup

NB: the 1909 edition was the first, the 1928 edition was the last
      
1909    Casuals       
1910    Clydesdale
1911    Casuals                3-0 Local Forces
1912    Southern               2-0 Local Forces
1913    Southern               2-1 Casuals
1914    Casuals            abd 2-1 Shamrock                [aet] [*]
1915    Casuals                3-1 Shamrock
1916      not held
1917    Queen's Park CC
1918    Queen's Park CC
1919      not held
1920    Maple
1921    Southern               5-2 Shamrock  
1922    St. Mary's             bt  Queen's Park CC 
1923    Sporting Club          4-3 STM
1924    Casuals                1-0 Sporting Club  
1925    Casuals
1926    Casuals
1927    Sporting Club          4-1 Casuals
1928    Maple                  2-0 Casuals   
[*] first match abandoned at 1-1 during extra time due to fading light

Number of Wins (18)

 7 Casuals

 3 Southern

 2 Maple
   Queen's Park CC
   Sporting Club  

 1 Clydesdale
   St. Mary's   

Allied Cup

  
1916    Queen's Park CC       

NB: 5 participants; Queen's Park CC won the competition unbeaten

Hugh McClelland/Gilbert Skinner Cup

  
NB: the 1919 edition was the first, the 1939 edition was the last

Hugh McClelland Cup
1919    North                    
1920    North
1921    North
1922    North
1923    North
1924    North
1925    North
1926    North
Gilbert Skinner Cup
1927    North
1928    North                  4-1 South
1929    South
1930    North
1931    North
1932    North
1933    North
1934    South                  1-0 North
1935    South
1936    North
1937    SAFL (Southern Amateur Football League)
1938    SAFL                   2-2 North
1939    North                    

Wilson Cup

  
NB: the 1911 edition was the first, the 1915 edition was the last;
    a cup with the same name was contested again in 1946

1911    Casuals                3-0 Shamrock          
1912    St Mary's
1913-14   not known
1915    Queen's Royal College  4-0 Shamrock

1946    Malvern

Sperling Cup

  
NB: between the champions of the Trinidad Amateur Football Association (TAFA) and
    those of the Southern Amateur Football Association (SAFA);
    the 1924 edition was the first, the 1932 edition was the last

1924    Shamrock               1-0 Tricentrol               
1925    Shamrock               bt  Trinidad Central Oilfields (TCO)  
1926    Brighton               2-1 Sporting Club
1927    Brighton               1-0 Maple 
1928    Maple                  2-0 Brighton     
1929    Casuals                3-0 Brighton 
1930    Everton                3-0 Casuals
1931    Everton
1932    Everton                                          

McKinney Cup

  
NB: the 1931 edition was the first, the 1932 edition was the last

1931    Everton                2-1 The Rest
1932    Everton                3-1 The Rest

Gooden Chisholm Cup

  
NB: the 1933 edition was the first, the 1975 edition was the last

1933    Queen's Royal College     
1934    Casuals
1935    Casuals       
1936    Sporting Club
1937    Leaseholds Club
1938    Apex
1939    Notre Dame             1-0 UBOT (United British Oilfields of Trinidad)
1940    Casuals                5-1 UBOT
1941    UBOT                   1-0 Casuals 
1942    Colts
1943    UBOT                   5-0 Fleet Air Arm 
1944    Shamrock
1945    UBOT
1946    Notre Dame
1947    Colts
1948    Malvern                3-0 UBOT   
1949    UBOT
1950    Maple
1951    Maple
1952    Maple
1953    United British Athletic Association    
1954    UBOT                   bt  Sporting Club  
1955    Sporting Club
1956    Notre Dame             1-0 Forest Reserve       
1957    Colts                  1-0 Shell    
1958    Shell
1959    Shamrock               0-0 TPD                     [trophy shared]
1960    Maple                  1-0 BP Palo Secco              
1961    Maple                  drw Shell                   [trophy shared]
1962    Maple
1963    Maple
1964    Paragon           
1965    Regiment               3-0 Shell
1966    Regiment
1967    Shell                  1-1 Maple                   [trophy shared]
1968    Caroni                 1-0 Malvern 
1969    Point Fortin CC        4-0 Malvern      
1970    Regiment               2-1 Maple 
1971      not held
1972    Point Fortin CC        1-1 Defence Force           [trophy shared]
1973      not held
1974    Malvern                drw Point Fortin CC         [trophy shared]
1975    Malvern                        

NB: Shell were renamed Point Fortin CC in 1968; 
    in 1934 Casuals won all available trophies, a performance emulated by Shamrock in 1959.

Wincairns Trophy

  
NB: the 1930 edition was the first, the 1932 edition was the last

1930    Everton
1931    Everton
1932    Everton

Hayward Shield

  
NB: the 1938 edition was the first

1938    TAFA                
1939      not held
1940    TAFA
1941    TAFA
1942    TAFA
1943    TAFA
1944    SAFL
1945    TAFA
1946    TAFA
1947    TAFA
1948    TAFA
1949    TAFA
1950    TAFA
1951    TAFA
1952    TAFA
1953    SAFL

Red Cross Cup

  
1934-55   not known 
1956    South                  2-0 North
1957    North                  3-2 South
1958    North 
1959    North East
1960    North
1961    North East
1962    North                  3-1 South
1963    North East
1964      [joint winners]
1965      not held
1966    South    

Roy Joseph Cup

  
1956    South                  3-0 North
1957    South
1958    South
1959    North East
1960    South
1961    South and North East [joint winners]
1962    South                  1-0 North
1963      [joint winners]
1964    South
1965    South
1966    North    

Hinds Memorial

  
NB: season opener

1956    South                  1-1 North
1957    North
1958    North
1959    North East
1960    North
1961    North East
1962    North East             2-2 South
1963    North East
1964    North

President's Cup

  
1965    Regiment               2-0 Police
1966    Regiment
1967    Juniors                3-1 Maple 
1968-69   not held
1970    Regiment               3-0 Maple
1971      not held
1972    Defence Force          4-0 [?]

POSL FL Cup

 
1965    Regiment and Malvern [joint winners]
1966    Maple
1967    Maple
1968    Paragon
1969    Malvern
1970    Regiment
1971    Paragon                drw Regiment                [trophy shared]
1972    Paragon  

Constantine Cup

1974    Malvern
1975    Malvern
1976      not known
1977    Malvern

League Cup

1985    Defence Force
1986-90   not held   
1991    Trintoc   
1992    Trintopec

FCB Cup

NB: league cup style competition sponsored by First Citizens Bank; format later
    changed to straight knock-out

1999    San Juan Jabloteh      bt  Williams Connection 
2000    San Juan Jabloteh      1-0 Defence Force 
2001    Williams Connection    1-0 Caledonia AIA
2002    Defence Force          2-0 Williams Connection
2003    San Juan Jabloteh      2-1 Williams Connection     [asdet]
2004    Williams Connection    2-2 Defence Force           [3-2 pen]
2005    Williams Connection    3-1 San Juan Jabloteh
2006    Williams Connection    3-1 North East Stars
2007    Williams Connection    2-0 Caledonia AIA
2008    Williams Connection    2-2 Joe Public              [6-5 pen]
2009    Defence Force          1-0 Joe Public           
2010    Joe Public             1-1 Defence Force           [3-0 pen]
2011    Caledonia AIA          2-1 TTEC
2012    Caledonia AIA          2-1 Defence Force
2013    Central                2-1 Defence Force   
2014    Central                1-0 North East Stars
2015    Williams Connection    2-1 Central
2016    Defence Force          1-0 Ma Pau Stars
2017    Williams Connection    3-1 Defence Force
2018    Central                2-2 Defence Force           [4-2 pen]
2019    Police                 4-1 La Horquetta Rangers

Number of Wins (21; lost finals between square brackets)

 8 [ 3] Williams Connection

 3 [ 7] Defence Force  
 3 [ 1] Central
 3 [ 1] San Juan Jabloteh 

 2 [ 2] Caledonia AIA

 1 [ 2] Joe Public
 1      Police

   [ 3] North East Stars [includes Ma Pau Stars]
   [ 1] La Horquetta Rangers
   [ 1] TTEC

Pro Bowl

NB: another league cup style competition inaugurated in 2005

2005    San Juan Jabloteh      1-0 Williams Connection
2006    San Juan Jabloteh      0-0 Williams Connection     [3-2 pen]
2007    Williams Connection    2-2 Superstar Rangers       [4-3 pen]
2008    Caledonia AIA          2-0 Defence Force
2009    Joe Public             1-1 Caledonia AIA           [5-3 pen]
2011    Joe Public             1-0 Williams Connection
2012    Defence Force          5-2 Caledonia AIA
2013    Williams Connection    0-0 North East Stars        [4-3 pen]   
2014    Williams Connection    3-0 Police
2015    Central                4-1 Caledonia AIA
2016    Defence Force          2-1 Williams Connection  
2017    Defence Force          2-2 Central FC              [5-3 pen]

Number of Wins (12; lost finals between square brackets)

 3 [ 4] Williams Connection
 3 [ 1] Defence Force  

 2      Joe Public
 2      San Juan Jabloteh 

 1 [ 3] Caledonia AIA
 1 [ 1] Central

   [ 1] North East Stars
   [ 1] Police
   [ 1] Superstar Rangers 


Number of League-Cup-and-Bowl Trebles (2)

 1 Joe Public                [2009]
 1 Williams Connection       [2014]

Lucozade Sport Goal Shield

2009    W Connection           3-0 Defence Force                    
2010    North East Stars       1-0 San Juan Jabloteh
2011      not played
2012    Caledonia AIA          3-1 Defence Force
2013    W Connection           0-0 North East Stars        [4-3 pen]
2014    Central FC             2-1 W Connection 
2015      not played
2016    Morvant Caledonia Utd. 2-2 W Connection            [4-1 pen]

NB: the 2009 edition was the first

Charity Shield

NB: between winners Digicel Pro League and Digicel Pro Bowl; in 2014 W Connection won both,
    Central entered as league runners-up

2012    W Connection           2-0 Defence Force     
2013    W Connection           4-2 Defence Force
2014    W Connection           1-0 Central FC 
2015    Central FC             1-0 W Connection    
2016    Defence Force          3-1 Central FC
2017      not played
2018    W Connection           7-1 North East Stars


Tobago FA Cup

2000    Grafton Stokely Vale   2-1 King David Enterprise Goal City
2001    Charlotteville Unifiers 
2002    FC Phoenix             1-1 St. Clair's C.S.        [5-4 pen]      
2003    Stokely Vale           2-1 Georgia                 [asdet]
2004    St. Clair's C.S.       2-0 Sidey's FC              
2005    Roxborough Lakers      3-2 Pepsi Hills United    
2006    St. Clair's C.S.       4-1 Charlotteville Unifiers
2007    Roxborough Lakers
2008    Roxborough Lakers      4-1 Charlotteville Unifiers
2009    Stokely Vale           2-0 1976 FC Phoenix
2010    St. Clair's C.S.       3-0 Mason Hill USSS    
2011    St. Clair's C.S.       9-0 Charlotteville Unifiers
2012    Roxborough Lakers      9-0 Hills United
2013    Bethel United          2-0 Lambeau
2014    Youth Stars United     2-0 Black Rock
2015    Sidey's FC             1-0 Goal City  
2016    Signal Hill United     5-1 Golden Lane
2017    Black Rock United
2018    Signal Hill United
2019    Stokely Vale           4-2 FC Goodwood
2020-21   presumably not held
2022    Black Rock United
2023    Stokely Vale           3-3 Sidey's FC              [5-4 pen]

About this document

Main sources: The Story of Football in Trinidad and Tobago 1893-2000, http://www.geocities.com/ronemrit/soccer.html

Prepared and maintained by Radek Jelínek and Hans Schöggl for the Rec.Sport.Soccer Statistics Foundation

Authors: Radek Jelínek and Hans Schöggl
Last updated: 14 Oct 2023

(C) Copyright Radek Jelínek, Hans Schöggl and RSSSF 2000/23
You are free to copy this document in whole or part provided that proper acknowledgement is given to the authors. All rights reserved.