Trinidad and Tobago football clubs have entered international competitions since 1967, when Regiment of the Port of Spain Football League took part in the 1967 CONCACAF Champions' Cup.^[1] Since the nation's first international club competition, several association football clubs from Trinidad and Tobago have entered North America, Central America, and Caribbean competitions (CONCACAF Champions' Cup/Champions League and CFU Club Championship).

The CONCACAF Champions' Cup started in 1962, but there was no Trinidad and Tobago representative during that inaugural season as the competition was open to eight teams from seven countries: Netherlands Antilles, Costa Rica, El Salvador, Guatemala, Haiti, Honduras, and México. Since their first appearance, Trinidad and Tobago clubs have claimed the Champions' Cup on two occasions with Defence Force winning the title in 1978 and again in 1985 in the Teteron Boys' treble-winning season.^[1]

Since the establishment of the CFU Club Championship in 1997, clubs from the Caribbean Islands that are members of the Caribbean Football Union, have competed in the region's qualification tournament for the CONCACAF Champions' Cup and Champions League. The first club to compete in the regional competition was United Petrotrin of the Semi-Professional League. The Oilmen won the inaugural tournament after defeating Seba United of Jamaica 2–1 to advance to the 1997 Champions' Cup. Since the country's first appearance in the CFU Club Championship, Trinidad and Tobago clubs have claimed the title on eleven occasions with an additional nine runners-up finishes.

Season	Team	Progress	Score	Opponents	Venue(s)
1962	None entered
1963	None entered
1967	Regiment	2nd in group stage		CRKSV Jong Colombia, Regiment, Somerset Trojans, Racing Club Haïtien
1968	None entered
1969	None entered
1970	Maple Club	First round	1–4	Transvaal
1971	None entered
1972	None entered
1973	None entered
1974	None entered
1975	None entered
1976	Tesoro Palo Seco	Second round	1–6	Voorwaarts
	Malvern United	Second round	0–2	Robinhood
1977	Defence Force	First round	0–4	Violette
	TECSA	Fourth round	2–4	Robinhood
1978	TECSA	First round	2–3	Voorwaarts
	Defence Force	Winners	4–1	Voorwaarts
1979	Tesoro Palo Seco	Third round	w/o	Robinhood
	Defence Force	Third round	2–3	CRKSV Jong Colombia
1980	Police	First round	2–4	Transvaal
	Defence Force	Second round	w/o	Robinhood
1981	Memphis	First round	0–3	SUBT
	Defence Force	First round	w/o	Transvaal
1982	Tesoro Palo Seco	First round	w/o	SUBT
	Defence Force	Third round	3–6	Robinhood
1983	Defence Force	First round	1–3	Robinhood
	Memphis	First round	4–5	SUBT
1984	Defence Force	First round	w/o	Violette
1985	Defence Force	Winners	2–1	Olimpia	2–0 at National Stadium, 0–1 at Estadio Francisco Morazán
1986	Sirocco	First round	2–4	Trintoc
	Trintoc	Semifinals	4–4 (3–4p)	Transvaal
1987	Trintoc	Semifinals	2–3	Defence Force
	Defence Force	Final	1–3	América	1–1 at National Stadium, 0–2 at Estadio Azteca
1988	Trintoc	First round	1–2	Excelsior
	Defence Force	Final	0–4	Olimpia	0–2 at Estadio Excélsior, 0–2 at Estadio Nacional
1989	Defence Force	3rd in group stage		FC Pinar del Río, Trintoc, Juventus, CRKSV Jong Colombia
	Trintoc	2nd in group stage		FC Pinar del Río, Defence Force, Juventus, CRKSV Jong Colombia
1990	None entered
1991	Defence Force	Third round	2–3	Police
	Police	Final	2–4	Puebla	1–3 at Estadio Cuauhtémoc, 1–1 at Skinner Park
1992	Trintoc	First round	1–2	Transvaal
	Mayaro United	Second round	1–2	Robinhood
1993	Hawks	First round	w/o	Sithoc
	Trintoc	Semifinals	0–1	Robinhood
1994	None entered
1995	None entered
1996	None entered
1997	United Petrotrin	Quarterfinals	0–1	D.C. United	Robert F. Kennedy Memorial Stadium
1998	Joe Public	Quarterfinals	0–8	D.C. United	Robert F. Kennedy Memorial Stadium
1999	Joe Public	Quarterfinals	0–2	Chicago Fire	Soldier Field
2000	Joe Public	Quarterfinals	0–1	Pachuca	Titan Stadium
2002	W Connection	Round of 16	0–3	Kansas City Wizards	0–1 at Manny Ramjohn Stadium, 0–2 at Arrowhead Stadium
	Defence Force	Round of 16	1–4	Pachuca	1–0 at Hasely Crawford Stadium, 0–4 at Estadio Hidalgo
2003	W Connection	Round of 16	5–6	Toluca	3–3 at Manny Ramjohn Stadium, 2–3 at Estadio Nemesio Díez
2004	San Juan Jabloteh	Quarterfinals	5–6	Chicago Fire	5–2 at Hasely Crawford Stadium, 0–4 at Soldier Field
2005	No clubs qualified for competition
2006	No clubs qualified for competition
2007	W Connection	Quarterfinals	2–4	Guadalajara	2–1 at Manny Ramjohn Stadium, 0–3 at Estadio Jalisco
2008	No clubs qualified for competition
2008–09	Joe Public	4th in group stage		Atlante, Montreal Impact, Olimpia
2009–10	San Juan Jabloteh	4th in group stage		Toluca, Marathón, D.C. United
	W Connection	3rd in group stage		UNAM, Comunicaciones, Real España
2010–11	San Juan Jabloteh	Preliminary round	0–6	Santos Laguna	0–1 at Marvin Lee Stadium, 0–5 at Estadio Corona
	Joe Public	4th in group stage		Santos Laguna, Columbus Crew, Municipal
2011–12	No clubs qualified for competition
2012–13	Caledonia AIA	3rd in group stage		Seattle Sounders FC, Marathón
	W Connection	3rd in group stage		Xelajú, Guadalajara
2013–14	W Connection	3rd in group stage		Árabe Unido, Houston Dynamo
	Caledonia AIA	3rd in group stage		Comunicaciones, Toluca
2014–15	No clubs qualified for competition
2015–16	Central FC	2nd in group stage		C.S.D. Comunicaciones, LA Galaxy
	W Connection	3rd in group stage		Deportivo Saprissa, Santos Laguna
2016–17	Central FC
	W Connection

Season	Team	Progress	Score	Opponents	Venue(s)
1997	United Petrotrin	Winners	2–1	Seba United	Palo Seco Velodrome
1998	San Juan Jabloteh	Quarterfinals	0–2	Aiglon du Lamentin	National Stadium
	Caledonia AIA	Final	0–1	Joe Public	Marvin Lee Stadium
	Joe Public	Winners	1–0	Caledonia AIA	Marvin Lee Stadium
2000	W Connection	2nd in final round		Joe Public, Harbour View, Carioca FC
	Joe Public	Winners		W Connection, Harbour View, Carioca FC
2001	W Connection	1st in final round		Racing Club Haïtien, CRKSV Jong Colombia
	Defence Force	Winners		Suriname National Lager, Roulado
2002	W Connection	Winners		Harbour View, US Robert
2003	W Connection	Final	3–3 (2–4p)	San Juan Jabloteh	1–2 at Manny Ramjohn Stadium, 2–1 at Hasely Crawford Stadium
	San Juan Jabloteh	Winners	3–3 (4–2p)	W Connection	2–1 at Manny Ramjohn Stadium, 1–2 at Hasely Crawford Stadium
2004	San Juan Jabloteh	Semifinals	1–2	Tivoli Gardens	1–1 at Hasely Crawford Stadium, 0–1 at Railway Oval
2005	North East Stars	Quarterfinals	w/o	Robinhood
2006	San Juan Jabloteh	Final	0–1	W Connection	Manny Ramjohn Stadium
	W Connection	Winners	1–0	San Juan Jabloteh	Manny Ramjohn Stadium
2007	San Juan Jabloteh	Third place	0–1	Puerto Rico Islanders	0–1 at Estadio Juan Ramón Loubriel, 0–0 at Hasely Crawford Stadium
	Joe Public	Final	1–2	Harbour View	Marvin Lee Stadium
2009	San Juan Jabloteh	Third place	2–1	Tempête	Marvin Lee Stadium
	W Connection	Winners	2–1	Puerto Rico Islanders	Marvin Lee Stadium
2010	San Juan Jabloteh	3rd in final round		Puerto Rico Islanders, Joe Public, Bayamón FC
	Joe Public	2nd in final round		Puerto Rico Islanders, San Juan Jabloteh, Bayamón FC
2011	Caledonia AIA	Second round	1–1 (2–3p)	Tempête	0–1 at Ato Boldon Stadium, 1–0 at Parc Levelt
	Defence Force	Semifinals	0–0 (2–4p)	Tempête	Providence Stadium
2012	W Connection	Final	1–1 (3–4p)	Caledonia AIA	Manny Ramjohn Stadium
	Caledonia AIA	Winners	1–1 (4–3p)	W Connection	Manny Ramjohn Stadium
2013	Caledonia AIA	Playoff round	3–2	Portmore United	1–0 at Hasely Crawford Stadium, 2–2 at Ato Boldon Stadium
	W Connection	1st in final round		Caledonia AIA, Antigua Barracuda FC
2014	Caledonia AIA	2nd in first round		Mirebalais, Waterhouse, Inter Moengotapoe
	Defence Force	2nd in first round		Alpha United FC, Harbour View
2015	Central FC	Winners	2–1	W Connection	Ato Boldon Stadium
	W Connection	Final	1–2	Central FC	Ato Boldon Stadium
2016	Central FC	Winners	3–0	W Connection	Stade Sylvio Cator
	W Connection	Final	0–3	Central FC	Stade Sylvio Cator

Since the inaugural season of the TT Pro League in 1999, the league champion and runners-up have entered the CFU Club Championship to earn qualification in the CONCACAF Champions' Cup/Champions League. The first Pro League club to compete in international competition was Joe Public when the club entered the 1999 CONCACAF Champions' Cup. However, the Eastern Lions qualified for the competition through the 1998 CFU Club Championship as a member of the Semi-Professional League the previous season. The 2000 CFU Club Championship was the first occurrence of clubs having earned qualification through final position in the Pro League. Defence Force entered as the 1999 Pro League champion, W Connection as runners-up, and Joe Public as the CFU Club Championship holders. Joe Public won the competition to provide the Pro League with its first international championship.

Pro League clubs have won the CFU Club Championship for Caribbean-based clubs on eleven occasions and nine additional runners-up finishes. However, no Pro League club has won the Champions' Cup or Champions League. The best performance occurred in the 2000, 2004, and 2007 Champions' Cup when Joe Public, San Juan Jabloteh, and W Connection, respectively, entered the quarterfinal round.

Note: The CONCACAF Champions' Cup began in 1962 and was renamed the CONCACAF Champions League in 2008–09 (abbreviated here to 2009). Trinidad and Tobago clubs began entering the continental competition in 1967. After the inauguration of the TT Pro League in 1999, teams from the Pro League were playing in CONCACAF competition during that season (abbreviated to 2009), even though they had actually qualified through the old Semi-Professional League the previous season.

Trinidad and Tobago finalists (1962–present)

For comparison, this table shows how Trinidad and Tobago clubs have performed at the top level of CONCACAF football before the TT Pro League era. Defence Force remains the only team from Trinidad and Tobago to win the Champions' Cup in 1978 and 1985.^[1] Since the Teteron Boys' treble-winning season, the best performance by a Trinidad and Tobago team came in 1987 and 1988 when Defence Force, and again in 1991 when Police finished as runners-up.

Club	Winners	Runners-up	Seasons won	Seasons runners-up
Defence Force	2	2	1978, 1985	1987, 1988
Police	0	1		1991

All finalists performance by club (1962–present)

On this table, covering before and during the TT Pro League era, the best-performing ten clubs are listed. Pro League club, Defence Force, is tied for ninth best-performing club in the CONCACAF Champions' Cup and Champions League.

Club	Winners	Runners-up	Seasons won	Seasons runner-up
Cruz Azul	5	2	1969, 1970, 1971, 1996, 1997	2009, 2010
América	5	0	1977, 1987, 1990, 1992, 2006
Pachuca	4	0	2002, 2007, 2008, 2010
Saprissa	3	2	1993, 1995, 2005	2004, 2008
UNAM	3	1	1980, 1982, 1989	2005
Monterrey	3	0	2011, 2012, 2013
Transvaal	2	3	1973, 1981	1974, 1975, 1986
Alajuelense	2	3	1986, 2004	1971, 1992, 1999
Olimpia	2	2	1972, 1988	1985, 2000
Toluca	2	2	1968, 2003	1998, 2006
Defence Force	2	2	1978, 1985	1987, 1988

All finalists performance by nation

For comparison, the following tables show the performance of all finalists in CONCACAF Champions' Cup and Champions League before and during the TT Pro League era. Although Trinidad and Tobago clubs performed well before the establishment of the TT Pro League, professional clubs have not reached the final of the continental competition.

Trinidad and Tobago performance (1962–present) Nation Winners Runners-up Mexico 29 14 Costa Rica 6 5 El Salvador 3 1 Suriname 2 8 Guatemala 2 3 Honduras 2 3 Trinidad and Tobago 2 3  United States 2 2 Haiti 2 0 Cuba 0 2 Curaçao 0 2

TT Pro League performance (2000–present) Nation Winners Runners-up Mexico 10 9 Costa Rica 2 2  United States 1 1 Honduras 0 1 Trinidad and Tobago 0 0

The Caribbean Football Union established the Caribbean Club Championship in 1997 as a qualification tournament for the CONCACAF Champions' Cup (later renamed the Champions League). The inaugural season of the TT Pro League was in 1999, so teams entering the regional competition based on Pro League finish began in 2000.

TT Pro League finalists (2000–present)

This table shows how Trinidad and Tobago clubs have performed in the CFU Club Championship since the start of the TT Pro League era. The table is currently headed by W Connection, with three wins, followed by Central FC (2), Morvant Caledonia United (1), Defence Force (1), Joe Public (1), and San Juan Jabloteh (1).

Club	Winners	Runners-up	Seasons won	Seasons runners-up
W Connection	3	6	2002, 2006, 2009	2000, 2001, 2003, 2012, 2015, 2016
Central FC	2	0	2015, 2016
Joe Public	1	2	2000	2007, 2010
San Juan Jabloteh	1	1	2003	2006
Morvant Caledonia United	1	0	2012
Defence Force	1	0	2001

Trinidad and Tobago finalists (1997–present)

This table combines the Trinidad and Tobago totals before and during the TT Pro League era. It shows that thanks to its earlier win in 1998, Joe Public, with two wins, have moved into second place, but still trail behind W Connection with three wins.

Club	Winners	Runners-up	Seasons won	Seasons runners-up
W Connection	3	6	2002, 2006, 2009	2000, 2001, 2003, 2012, 2015, 2016
Joe Public	2	2	1998, 2000	2007, 2010
Central FC	2	0	2015, 2016
Morvant Caledonia United	1	1	2012	1998
San Juan Jabloteh	1	1	2003	2006
Defence Force	1	0	2001
United Petrotrin	1	0	1997

All finalists' performance by club (1997–present)

On this table, covering before and during the TT Pro League era, the best-performing Pro League club, W Connection, is also the best-performing club in the CFU Club Championship ahead of fellow Pro League clubs Joe Public and Central FC, Puerto Rico Islanders, and Jamaican club Harbour View.

Club	Winners	Runners-up	Seasons won	Seasons runners-up
W Connection	3	6	2002, 2006, 2009	2000, 2001, 2003, 2012, 2015, 2016
Joe Public	2	2	1998, 2000	2007, 2010
Puerto Rico Islanders	2	1	2010, 2011	2009
Central FC	2	0	2015, 2016
Harbour View	2	0	2004, 2007
Morvant Caledonia United	1	1	2012	1998
San Juan Jabloteh	1	1	2003	2006
Portmore United	1	0	2005
Defence Force	1	0	2001
United Petrotrin	1	0	1997
Tempête	0	1		2011
Robinhood	0	1		2005
Tivoli Gardens	0	1		2004
Arnett Gardens	0	1		2002
Seba United	0	1		1997

All finalists' performance by nation

For comparison, the following tables show the performance of all finalists in the CFU Club Championship before and during the TT Pro League era, when Trinidad and Tobago were narrowly in first place in terms of number of wins, compared to having by far the most finalists compared to other nations.

Trinidad and Tobago performance (1997–present) Nation Winners Runners-up Trinidad and Tobago 11 10 Jamaica 3 3 Puerto Rico 2 1 Haiti 0 1 Suriname 0 1

TT Pro League performance (2000–present) Nation Winners Runners-up Trinidad and Tobago 9 9 Jamaica 3 2 Puerto Rico 2 1 Haiti 0 1 Suriname 0 1