In 2010 FIFA World Cup™ qualifying, the small island nation of Bermuda were staged to pull-off one of the biggest upsets in the North, Central America, and Caribbean region. After struggling to see off the Cayman Islands in round one of CONCACAF qualifying, the Gombey Warriors took on Caribbean giants Trinidad and Tobago. Expected to ease past the Bermudan nation, the Soca Warriors entered the first leg of the second round with little to worry about. However, goal-poacher John Barry Nusum had other ideas, scoring twice to inflict a shock defeat upon T&T before a stunned crowd in Macoya. Bermuda failed to live up to upset-expectations, though, as T&T pulled their side together to limp past their minnow rivals with a 2-0 win in the second leg.

In qualifying for Brazil 2014 Bermuda came back to haunt T&T once again. Led by captain Khano Smith and veteran striker Nusum, they again beat the Warriors in the first group stage only to fall short and finish third in their group, just three points off the pace of winners Guyana.

Best performance in a FIFA competition:
None
Former stars: Shaun Goater, Kyle Lightbourne, Clyde Best