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Typography
A List of TnT Digicel Charity Shield Champions Since 2009 with Inshan "Flex" Mohammed.

Year - Winners - Runners-Up -Venue.

2009 - W Connection 3 (Jonathan Frias 14, 74, Andre Toussaint 59) v Defence Force 0, Manny Ramjohn Stadium.

2010 - North East Stars 1 (Sean Frazer 77) v San Juan Jabloteh 0, Marvin Lee Stadium.

2011 - Caledonia AIA 3 (Kareem Joseph 3-Pen, Jamal Gay 49, Walter Moore 50) v Defence Force 1 (Richard Roy 40), Hasley Crawford Stadium.

2012 - W Connection 0 v North East Stars 0, Marvin Lee Stadium.
After Penalties - W Connection 4 (Joevin Jones, Termain Shayn Paul, Jomal Williams, Clyde Leon) v North East Stars 3 (Elton John, Kareem Moses, Kennedy Hinkson).

2013 - Central FC 2 (Rundell Winchester 13, Marvin Oliver 19) v W Connection 1 (Joevin Jones 21), Ato Boldon Stadium.

2014 - W Connection (Hashim Arcia 39) v Central FC 0, Ato Boldon Stadium.

2015 - Central FC 1 (Andre Ettienne 67) v W Connection 0, Ato Boldon Stadium.

2015/16 - Morvant Caledonia United 2 (Sheldon Holder 15, 82) v W Connection 2 (Shahdon Winchester 2, Andre Toussaint 53), Hasely Crawford Stadium.
After Penalties - Morvant Caledonia United 4 (Kareem Joseph, Akim Armstrong, Sheldon Holder, Pernell Schultz) v W Connection 1 (Hughtun Hector)

2016/17 - Central FC 2 (Darren Mitchell 3, Kenwyne Jones 5) v Defence Force 2 (Devorn Jorsling 18, Sean Narcis 89), Ato Boldon Stadium
After Penalties - Central FC 2 (Leston Paul, Sean De Silva, Nicholas Dillon) v Defence Force 1 (Devorn Jorsling)

2016/17 - Cancelled.

2018 - W Connection 7 (Marcus Joseph 8, 30, 48, Dimitri Apai 34, Kadeem Corbin 51, Briel Thomas 61, Adan Noel 69) v North East Stars 1 (Jaden Prowell 71-Pen.), Ato Boldon Stadium

2019 - Cancelled.

2020 - Tournament cancelled because of the worldwide pandemic, the Coronavirus (COVID-19).