Trinidad & Tobago

1970s

At the 1973 CONCACAF Championship, Trinidad and Tobago fell two points short of qualifying for the 1974 World Cup in controversial fashion. Trinidad and Tobago lost a crucial game on 4 December 1973 against hosts Haiti 2–1 after being denied five goals. The referee, José Roberto Henríquez of El Salvador, and Canadian linesman James Higuet were subsequently banned for life by FIFA for the dubious events of the match.

1980s to 1990s: The Strike Squad

Trinidad and Tobago came within one game of qualifying for the 1990 World Cup in Italy. Nicknamed the "Strike Squad" during the qualifying campaign, Trinidad and Tobago needed only a draw to qualify in their final game played at home against the United States on 19 November 1989. In front of an over-capacity crowd of more than 30,000 at the National Stadium on "Red Day", Paul Caligiuri of the United States scored the only goal of the game in the 38th minute dashing Trinidad and Tobago's qualification hopes. For the good behaviour of the crowd at the stadium, despite the devastating loss and overcrowded stands, the spectators of Trinidad and Tobago were awarded the FIFA Fair Play Award in 1989.

2000s

2006 FIFA World Cup

Trinidad and Tobago qualified for the 2006 World Cup in Germany, its first-ever qualification for the tournament. During their qualifying campaign, they sat at the bottom of the table in the final round of qualifying with one point from three. However, after the arrival of Leo Beenhakker as team coach and the recalling of veteran players Dwight Yorke and Russell Latapy, Trinidad and Tobago reversed its fortunes and placed fourth in the group. They qualified via a play-off against Bahrain, recovering from a 1–1 draw at home to win 1–0 in Manama, Bahrain to book a place in the finals. As a result, Trinidad and Tobago became the smallest country to qualify for the FIFA World Cup, a record they held until Iceland reached their first World Cup in 2018.

In Germany, Trinidad and Tobago were grouped with England, Sweden and Paraguay in Group B.They played their initial game, drawing 0–0 against Sweden, even though they were reduced to ten men early in the second half. They faced losses in their remaining matches against England and Paraguay, each by a 2–0 margin.

2010s

2010 World Cup Cycle

Trinidad and Tobago began their campaign in the second round against Bermuda. Trinidad and Tobago lost the first match 2–1 at home, but bounced back to win the away leg 2–0 to progress to the third round 3–2 on aggregate. The Soca Warriors entered Group 1 alongside the United States, Guatemala, and Cuba. They then progressed to the Hexagonal round, finishing second in the group with eleven points from six games. There they faced Costa Rica, El Salvador, Honduras, Mexico and the United States. The group began badly for Trinidad and Tobago as they drew 2–2 with El Salvador after leading 2–0, and then drew 1–1 with Honduras. Three consecutive losses, to the United States, Costa Rica and Mexico, put the Soca Warriors in last place with two points from five matches. After defeating El Salvador 1–0, they suffered further losses to Honduras and the United States the following month, ending their hopes of qualifying, and they eventually finished bottom of the group.

2014 World Cup Cycle

Trinidad and Tobago entered qualification for the 2014 World Cup in the second round as a seeded team, with Guyana, Bermuda and Barbados also drawn in Group B. The Soca Warriors defeated Bermuda (1–0) and Barbados (2–0) in their first two matches. However, on 7 October 2011, they lost away to Bermuda in Devonshire Parish 2–1. The team recovered four days later by defeating Barbados 4–0 in the Hasely Crawford Stadium with a hat-trick from Lester Peltier. Entering the final two matches in the Second Round, Trinidad and Tobago were in second place, behind Guyana by one point. As only the group winners would advance to the third round, the Soca Warriors needed to take four points in the two matches against Guyana to advance. Trinidad and Tobago first traveled to Providence, Guyana to face the Golden Jaguars on 11 November 2011. With an early goal from Ricky Shakes and another from Leon Cort in the 81st minute, Trinidad and Tobago trailed 2–0 and faced elimination. Kenwyne Jones pull a goal back in the 93rd minute, but the match ended 2–1 to Guyana. On 12 January 2012, Otto Pfister was sacked after the country's earliest exit from World Cup qualification since 1994.

2018 World Cup Cycle

Trinidad and Tobago entered qualification for the 2018 FIFA World Cup in the fourth round and were drawn into Group C with Guatemala, Saint Vincent and the Grenadines, and the United States. The team finished second in the group with 11 points to qualify for the Hexagonal. However, they finished in sixth place in the final round with only six points, even though they eliminated the United States from World Cup contention with a 2–1 victory in the final match.