| 1 | A | B | C | D | E | F | G |
| --- | --- | --- | --- | --- | --- | --- | --- |
| 2 | List of TT Pro League seasons - Seasons |  |  |  |  |  |  |
| 3 | Season | Champions (number of titles) | Caribbean Club Championship | Withdrew from the TT Pro League | Admitted to the TT Pro League | Top goalscorer | Top goalscorer |
| 4 | Season | Champions (number of titles) | Caribbean Club Championship | Withdrew from the TT Pro League | Admitted to the TT Pro League | Player(s) | Goals |
| 5 | 1999 | Defence Force | W Connection | FUTGOF Point Fortin Civic | Arima Fire Caledonia AIA | Trinidad and Tobago Arnold Dwarika (Joe Public) | 45 |
| 6 | 2000 | W Connection | Defence Force | - | - | Trinidad and Tobago Jason Scotland (Defence Force) | 22 |
| 7 | 2001 | W Connection (2) | - | Doc's Khelwalaas Police | North East Stars South Starworld Strikers | Unknown | - |
| 8 | 2002 | San Juan Jabloteh | W Connection | - | South West Institute of Football Tobago United | Trinidad and Tobago Sean Julien (South Starworld Strikers) | 16 |
| 9 | 2003–04 | San Juan Jabloteh (2) | - | Joe Public | - | Guyana Randolph Jerome (North East Stars) | 28 |
| 10 | 2004 | North East Stars | - | South Starworld Strikers | - | Trinidad and Tobago Jerren Nixon (North East Stars) | 37 |
| 11 | 2005 | W Connection (3) | San Juan Jabloteh | - | Joe Public South Starworld Strikers Superstar Rangers | Brazil Gefferson (W Connection) | 14 |
| 12 | 2005 | W Connection (3) | San Juan Jabloteh | - | Joe Public South Starworld Strikers Superstar Rangers | Saint Lucia Earl Jean (W Connection) | 14 |
| 13 | 2006 | Joe Public | San Juan Jabloteh | South Starworld Strikers | Police | Jamaica Roen Nelson (Joe Public) | 16 |
| 14 | 2006 | Joe Public | San Juan Jabloteh | South Starworld Strikers | Police | Trinidad and Tobago Anthony Wolfe (San Juan Jabloteh) | 16 |
| 15 | 2007 | San Juan Jabloteh (3) | Joe Public | Police | Ma Pau | Antigua and Barbuda Peter Byers (San Juan Jabloteh) | 15 |
| 16 | 2008 | San Juan Jabloteh (4) | W Connection | North East Stars | Police FC South End | Trinidad and Tobago Devorn Jorsling (Defence Force) | 21 |
| 17 | 2009 | Joe Public (2) | San Juan Jabloteh | United Petrotrin | North East Stars | Trinidad and Tobago Kerry Baptiste (Joe Public) | 35 |
| 18 | 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 |
| 19 | 2011–12 | W Connection (4) | Caledonia AIA | San Juan Jabloteh | Central FC | Trinidad and Tobago Richard Roy (Defence Force) | 15 |
| 20 | 2012–13 | Defence Force (3) | Caledonia AIA | T&TEC | Point Fortin Civic San Juan Jabloteh | Trinidad and Tobago Devorn Jorsling (Defence Force) | 21 |
| 21 | 2013–14 | W Connection (5) | Central FC | - | - | Trinidad and Tobago Marcus Joseph (Point Fortin Civic) | 16 |
| 22 | 2014–15 | Central FC | W Connection | - | Club Sando | Trinidad and Tobago Devorn Jorsling (Defence Force) | 21 |
| 23 | 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).