The Trinidad and Tobago national football team holds the record for being the smallest nation, both in size and population, to ever qualify for the world cup finals. They began entering world cup qualifiers in 1966 and have entered all subsequent tournaments.
In 1974 the Trinidad and Tobago national football team came very close to qualification. They ended up falling two points short of making it to the tournament. They lost a game against Haiti but were denied five goals in the match. The referee and a linesman were both banned for life by FIFA after the game.
They were close again in 1990 when they needed only a draw in their last qualifying match against the United States. They ended up losing the game in front of a packed 30,000 home audience.