Despite a rich history in football, the Caribbean has not had many moments to savour on the World stage, making them, interestingly, all the more special.

Cuba provided the first of the moments, making the quarterfinals of the FIFA World Cup all the way back in 1938.

Cuba had always been a little special island, long proving itself self-sufficient and able to compete with the rest of the world, despite any political or financial issues that could serve to slow its development.

That self-sufficiency and ability to achieve despite significant odds meant that Cuba’s entrance to the FIFA World Cup was not a emblematic moment and the rest of the Caribbean felt no closer to the possibility of making it on the world stage.

Thirty-six years later, Haiti provided the second moment, getting to the FIFA World Cup in 1974.

That feat, for a country, which had long-standing political issues and an overbearing poverty problem, was immense.

Now the rest of the Caribbean began to take note. Maybe now other islands could dare to dream.

While Haiti’s football has ebbed and flowed and they have not quite gotten back to those heady heights, the moment was important.

All of a sudden, the possibilities for Caribbean football were immense.

But it took another 20 years before the Reggae Boyz were on a similar journey. For the first time, CONCACAF had more than the obligatory two spots that would go to Mexico and the United States.

Now there was hope for someone else to join the fray. Still there were obstacles.

In 1997, the Reggae Boyz were up against it. In the final round they were winless, until a series of three games, 1-0 wins over each of El Salvador, Canada, and Costa Rica.

After finishing winless in the first four games of the final qualifying round, Jamaica recorded three 1–0 wins over El Salvador, Canada, and Costa Rica, giving them a chance at history.

Jamaica were on the cusp of becoming the first English-speaking team from the Caribbean to make it to the World Cup.

But standing in their way was the mighty Mexico. Jamaica needed to avoid losing to a team they had lost to 6-0 earlier in those qualifiers. There was hope but it was slim.

History has a funny way of staying the same and no matter how many times this story gets told, the 0-0 draw the Reggae Boyz achieved against the attacking juggernauts that were Mexico still seems unlikely.

An entire nation celebrated, but so did the rest of the Caribbean. After all, there were other countries in the region that had proven worthy adversaries for the Reggae Boyz and that meant somebody else could make it too.

In 2006, somebody else did.

Trinidad and Tobago, still with two of its legends, Dwight Yorke and Russell Latapy, in tow would take an ageing team, and prove the Caribbean were now becoming a force to be reckoned with.

Until 2018 when Iceland made their World Cup bow, T&T were the smallest nation to ever play in the tournament.

But it wasn’t easy either, and Trinidad and Tobago, after finishing fourth in the final round had to contend with the unknown quantity that was Bahrain.

The tiny twin-island republic had to play against a team, which had financial resources that would dwarf it.

Things looked even more bleak for T&T after the first leg of the home-and-away tie on November 12, 2005, played at the Hasely Crawford Stadium, ended 1-1.

This meant, T&T had to go away to win against a team they couldn’t get the better of at home.

Again, the Caribbean beat the odds and a 1-0 win at the Bahrain National Stadium on the 16th of November 2005 again changed the course of history for the Caribbean side and the region around it.

The Caribbean has, since those moments made great leaps in the transport of its players all over the world, even if those marginal improvements have yet to bare fruit in terms of consistent Caribbean representation at the ICC World Cup.

But the improvements continue as can be seen with the large number of locally grown players, now turning out for the national teams of countries all over the region.

Today there is more and more competition from the rest of the Caribbean and neither T&T nor Jamaica have a free run of the region anymore.

It is interesting that the success of the three over the last 46 years, is what has created a competitive Caribbean and destroyed the spectre of their unquestioned dominance.  

Former Manchester United star and Trinidad & Tobago’s most successful footballer, Dwight Yorke paints a picture of frustration at not being able to contribute to the development of sport in his country.

According to Yorke, a member of T&T 2006 World Cup team to Germany, he remains available to give back in whatever way he can.

“I would always love to contribute to my country the experience that I’ve gained at the level I’ve played at for so many years. You would’ve thought I would’ve been involved in Trinidad and Tobago football, certainly in the future,” said Yorke during an interview with T&T radio station i95FM.

Yorke explained that he was fortunate to have been given much from the sport of football and would only be too happy to give back.

However, Yorke said, there has never been an approach for such an occurrence to take place.

“I've always wanted to contribute to my country, I always want to help. I feel that with the experience and knowledge I've got, I could certainly help out in some capacity. However, that hasn't happened, I haven't been approached," he said.

The former striker, who scored 27 times in 72 appearances for the Soca Warriors says, the problem is not one he faces alone, with stars like Brian Lara and Russell Latapy finding it difficult to make their marks.

"It does make me feel a little bit concerned that someone like Brian Lara, who is the most accomplished cricketer in the West Indies, hasn't got a role in West Indies cricket," said Yorke.

“[…] the reality is there is no greater accomplishment than Lara, Latapy and myself. Why would you not use that to your benefit? I find that very, very strange, when other countries would love to use our expertise in trying to find out what it takes, what it means ... to be out there.

Trinidad & Tobago have been stripped of two Pan American Games 2019 medals after Pan Am Sports revealed in a press release that two of the country’s cyclists tested positive for drugs during the Lima, Peru event.

T&T won three medals at the Pan Am games but may now have to return its team cycling gold and an individual cycling medal, with Nicholas Paul’s individual sprint gold the only accolade that remains.

According to reports, T&T have hit back at the Pan Am Games, saying the organisers have breached confidentiality protocol in announcing the decision to rescind the gold medals and had already put the matter before a judiciary panel.

"The information put out by Pan American Sports is currently being challenged by Trinidad and Tobago. Any discussion of reallocation of medals is premature due to the number of things currently being ventilated," said T&T’s team lawyer Tyrone Marcus.

However, Pan Am Sports Secretary-General, Ivar Sisniega insists that no protocols were breached and remained confident that his organisation’s ruling would be allowed to stand.

“We have been very careful with the issue of doping at the Pan American Games of Lima 2019, respecting all the corresponding protocols and processes. After our executive committee meeting, we have officially approved the decisions of the disciplinary commission and the respective disqualifications of the athletes involved, and this has generated the changes we are reporting today. With this, we close the medal table of our Games,” said Sisniega.  

The official draw for the qualifying matches of the 2021 Concacaf Gold Cup is in the books and Haiti, Trinidad & Tobago, Bermuda and Cuba, despite already being placed in round two, are not set to have an easy of it.

As announced in March of 2018, the 2019-2020 Concacaf Nations League kicked off the road to 2021 Concacaf Gold Cup. After group stage play, the top two finishers in each of the League A groups and the top finisher in each of the League B groups secured their participation in the 16th edition of the Confederation’s premier tournament for men’s national teams.

 

The road to the 2021 Concacaf Gold Cup will continue next year with a two-round qualifier, to be played in a direct elimination format. Beginning in March of 2020, the second-place finishers of League B will face the first-place finishers of League C. The four matchups were drawn as follows:

 

Matchup 1: Guadeloupe vs Saint Vincent and the Grenadines

Matchup 2: Barbados vs Guyana

Matchup 3: Bahamas vs French Guiana

Matchup 4: Guatemala vs Monserrat

 

After home-and-away play, the four round one matchup winners will advance to the second round, where they will face the third-place finishers of League A. The second round will take place during the FIFA window of June 2020. The four round-two matchups were drawn as follows:

 

Matchup 5: Winner Matchup 1 vs Haiti

Matchup 6: Winner Matchup 2 vs Trinidad & Tobago

Matchup 7: Winner Matchup 3 vs Bermuda

Matchup 8: Winner Matchup 4 vs Cuba

 

This mean Haiti will play against either Guadeloupe or St Vincent and the Grenadines, while Trinidad & Tobago has the task of trying to turn back either Barbados or Guyana. Bermuda, who have done well to date, have either the Bahamas or the dangerous French Guiana, while Cuba must contend with either Guatemala or Montserrat.

After home-and-away play, the four matchup winners will qualify for the 2021 Concacaf Gold Cup, joining (in alphabetical order); Canada, Costa Rica, Curacao, El Salvador, Grenada, Honduras, Jamaica, Martinique, Mexico, Panama, Suriname and the United States.

The gala event in Miami, FL was attended by Concacaf President Victor Montagliani, Concacaf General Secretary Philippe Moggio and the presidents of all 41 Concacaf Member Associations.

The draw was conducted by Concacaf Development Director Jason Roberts and Concacaf Director of Competitions Carlos Fernandez.

The complete schedule, including dates, kickoff times and host venues for the qualifying matches will be announced at a later date.

 

Honduras had already clinched a spot in the Nations League finals next summer heading into the final match of group play, but they didn’t let up in the closer against Trinidad and Tobago, putting up an impressive 4-0 win.

Jonathan Rubio got Los Catrachos off to a flying start, sending a powerful strike from 20 yards out past a diving Marvin Phillip in the 5th minute.

Honduras continued to dominate the early proceedings, culminating in a 20th minute goal from Brayan Moya to double the lead.

Moments before the halftime whistle, Rubio was brought down for a penalty, and Alberth Elis converted in the 45+2 minute.

The second half was more of the same story; Elis netted his second of the day in the 53rd minute to complete the scoreline.

Trinidad did have some shots on goal, but none got past Luis Lopez who ended the day with four saves.

The victory means Honduras finish the group stage with 10 points, and are likely to enter the knockout round as the #2 seed. On the other end, the defeat means Trinidad and Tobago have been relegated to League B and will enter the Gold Cup qualifiers in the second round.

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