There was no meaningful regional competition until the Shell Cup. We played a lot of foreign teams on winter break. We started playing WC since 66. I think we joined Concacaf in 62. We used to play occasional non-competitive games against Caribbean and Central teams. When we started in Concacaf, We found the going rough. We were competitive, but the Central Americans professionalism most of the time over came TT. Is only from 74 TT started to challenge the Central Americans. We were on par with Cuba, Haiti, Suriname and Jamaican, US, Canada. Suriname and Haitian clubs did very well in the Concacaf club competition. Violet, Robin Hood, Transval. DF did extremely well also. And Police was did have a short run.
As far as national teams. in the 70s Haiti, TT and Suriname were the best in the Caribbean. Later on JA improved and did qualify for WC. The problem with TT is always consistency. We could never put 2 runs at WC, PanAm or CAC games. Our Chart will look like high peak, then a 15 year flat plain and then a high peak. There are many reasons for this. The chief being not able to have money for developmental football. Money to prepare teams effectively. Give the players a reasonable stipend while doing national duty. Plus we had a 30 yr Jack Warner debacle.
We have produced some extremely good players. In the beginning they all went to the US and some did enjoyed great success. England and Europe were not ready for Caribbean players. At least the 1st divisions. Clyde Best from Bermuda was an exception to the rule. Steve David, Archibald, Deleon won MVP. Gally, Ray Moraldo, Tony Douglas won NASL championships. Lincoln did extremely well at pro and college level.
Right now, it mass confusion. As a famous TT politician once said. "Wake me up when it over".