List of TT Pro League seasons
Seasons

Season
Champions (number of titles)
Caribbean Club Championship
Withdrew from the TT Pro League
Admitted to the TT Pro League
Top goalscorer
Top goalscorer
Season
Champions (number of titles)
Caribbean Club Championship
Withdrew from the TT Pro League
Admitted to the TT Pro League
Player(s)
Goals
1999
Defence Force
W Connection
FUTGOF Point Fortin Civic
Arima Fire Caledonia AIA
Trinidad and Tobago Arnold Dwarika (Joe Public)
45
2000
W Connection
Defence Force
-
-
Trinidad and Tobago Jason Scotland (Defence Force)
22
2001
W Connection (2)
-
Doc's Khelwalaas Police
North East Stars South Starworld Strikers
Unknown
-
2002
San Juan Jabloteh
W Connection
-
South West Institute of Football Tobago United
Trinidad and Tobago Sean Julien (South Starworld Strikers)
16
2003–04
San Juan Jabloteh (2)
-
Joe Public
-
Guyana Randolph Jerome (North East Stars)
28
2004
North East Stars
-
South Starworld Strikers
-
Trinidad and Tobago Jerren Nixon (North East Stars)
37
2005
W Connection (3)
San Juan Jabloteh
-
Joe Public South Starworld Strikers Superstar Rangers
Brazil Gefferson (W Connection)
14
2005
W Connection (3)
San Juan Jabloteh
-
Joe Public South Starworld Strikers Superstar Rangers
Saint Lucia Earl Jean (W Connection)
14
2006
Joe Public
San Juan Jabloteh
South Starworld Strikers
Police
Jamaica Roen Nelson (Joe Public)
16
2006
Joe Public
San Juan Jabloteh
South Starworld Strikers
Police
Trinidad and Tobago Anthony Wolfe (San Juan Jabloteh)
16
2007
San Juan Jabloteh (3)
Joe Public
Police
Ma Pau
Antigua and Barbuda Peter Byers (San Juan Jabloteh)
15
2008
San Juan Jabloteh (4)
W Connection
North East Stars
Police FC South End
Trinidad and Tobago Devorn Jorsling (Defence Force)
21
2009
Joe Public (2)
San Juan Jabloteh
United Petrotrin
North East Stars
Trinidad and Tobago Kerry Baptiste (Joe Public)
35
2010–11
Defence Force (2)
Caledonia AIA
Joe Public Ma Pau FC South End Tobago United
T&TEC
Trinidad and Tobago Devorn Jorsling (Defence Force)
15
2011–12
W Connection (4)
Caledonia AIA
San Juan Jabloteh
Central FC
Trinidad and Tobago Richard Roy (Defence Force)
15
2012–13
Defence Force (3)
Caledonia AIA
T&TEC
Point Fortin Civic San Juan Jabloteh
Trinidad and Tobago Devorn Jorsling (Defence Force)
21
2013–14
W Connection (5)
Central FC
-
-
Trinidad and Tobago Marcus Joseph (Point Fortin Civic)
16
2014–15
Central FC
W Connection
-
Club Sando
Trinidad and Tobago Devorn Jorsling (Defence Force)
21
2015–16
Central FC (2)
San Juan Jabloteh
-
-
Trinidad and Tobago Makesi Lewis (Police)
21

Question: Which six clubs have won the TT Pro League title, and how many have they won each?
Answer: Six clubs have won the TT Pro League title, which are W Connection (5 times), San Juan Jabloteh (4), Defence Force (3), Central FC (2), Joe Public (2), and North East Stars (1) with W Connection being the first team to win consecutive titles (2000 to 2001).