Dwight Yorke hopes the newly-launched British Airways Tobago Football Legends Challenge will provide a major boost for the country which has struggled to build upon its first-ever qualification for a FIFA World Cup in 2006.
The event, which sees 64 former English Premier League players compete in a six-a-side tournament at stadium in Tobago named after Yorke, will take place from June 15 to 22, 2015.
The former Manchester United, who also played for Aston Villa, Blackburn Rovers, Birmingham City and Sunderland during his illustrious career, was captain for Trinidad and Tobago's three group stage matches in Germany more than eight years ago.
The 43-year-old was recently quoted as saying that football in the country had since taken "a turn for the worst in many respects" by the Trinidad Guardian Newspaper.
Trinidad and Tobago failed to secure a spot at both the 2010 and 2014 World Cups in South Africa and Brazil respectively, and Yorke believes the success of 2006 led to complacency setting in. 
"I think it's the mentality sometimes of our country," Yorke, Tobago's global brand ambassador, told insidethegames here.
"It was mainly our own downfall at the time.
"Our country has a population of 1.3 million people and to qualify for the World Cup was obviously a historical moment.
"I've been fortunate to play at the highest level and as a player, you will not get any higher accolade than representing your country in a World Cup.
"So that was huge and I felt that at that time, instead of embracing it and learning from it, and making sure we continued going in the right direction, I feel that we took our eye off the ball.
"Maybe the players themselves to a certain extent are to blame with that success.
"They didn't embrace it well.
"They took it for granted.
"I always feared the worst because I could see from my own eyes that this was going to go belly up, and it did go belly up."
As well as British Airways, the Football Legends Challenge is also supported by the Professional Footballers' Association (PFA) and the Trinidad and Tobago Football Association.
Former players from Manchester United, Chelsea, Arsenal, Tottenham and Liverpool will be joined by All-Star teams formed from the Caribbean and the PFA.
The eighth and final team will come from either Newcastle, Everton, Aston Villa or Leicester.
The legends will also compete in a golf tournament at the Magdalena Grand Beach and Golf Resort on June 19, as a prelude to the launch of the Dwight Yorke International Golf Tournament in 2016.
The Resort is home to Tobago's 18-hole Professional Golfers' Association (PGA) designed championship course.
Sky Sports will broadcast the Football Legends Challenge in a 90-minute special.