On Friday night, the United States national team will take on Antigua & Barbuda (7 pm ET, beIN Sport, live chat on MLSsoccer.com) in a game that will go a long way toward sending the US to the final round of CONCACAF World Cup qualifying — should they get the three points expected of them, of course.
With three teams sitting on seven points in Group A and Jamaica or Guatemala set to take points off the other when the two square off in Guatemala City, the US could separate themselves from the pack and all but secure a spot in the Hexagonal.
And while the stakes are high, this is far from the first crunch qualifier in the Caribbean the national team has faced. Though games in Central America and Mexico have traditionally presented the toughest challenges, the Yanks have faced crucial games at Caribbean opponents in nearly every qualifying cycle, matchups that have provided some of the most memorable moments in American soccer's recent history.
Here are the top three:
1989: Trinidad & Tobago, final round
It was American soccer’s version of the "Shot Heard ‘Round the World." Mexico’s disqualification from the 1990 World Cup opened the door for the Americans to snap their 40-year World Cup drought, but it wasn't an easy task by any means.
After a 0-0 home draw against El Salvador, the United States traveled to Trinidad & Tobago to face a side boasting soon-to-be stars Dwight Yorke and Russell Latapy, needing a result to book their ticket to Italy.
In front of a raucous crowd at Port of Spain’s National Stadium, the US weathered intense pressure from the home side, who were also looking to earn their first trip to soccer’s biggest stage. But, much to the home fans' chagrin, an unlikely hero appeared in the form of Paul Caligiuri.
The defensive midfielder, not known for his goalscoring abilities, picked up a square pass from Tab Ramos, beat a man and looped an awkward shot that bounced just under T&T goalkeeper Michael Maurice at the half-hour mark.
The final hour proved harrowing for the US, but they managed to hold on and secure qualification in the final game, sparking wild celebrations (pictured above). Following Italia ’90, the team has qualified for every World Cup since.
2000: Barbados, semifinal round
The USA’s magical run to the 2002 World Cup quarterfinals almost wasn’t.
An inconsistent performance in a semifinal round left the US in second place going into the final matchday, just one point ahead of Guatemala in a group also containing Costa Rica and Barbados. That meant a US draw or loss to the Caribbean side and a Guatemalan win would result in an embarrassing elimination.
Guatemala did indeed win, impressively topping Costa Rica 2-1 at home with a brace from future LA Galaxy star Carlos Ruiz. Meanwhile, over in Bridgetown, things were looking dicey for the US, with a 0-0 scoreline at the hour mark meaning they were less than a half-hour away from being knocked out before the final round.
But Clint Mathis finally struck in the 63rd minute, and the US piled on the goals late on, netting three more times to send the team through to the Hex, where they posted the win over Mexico that became famously known simply as "Dos a cero," and laid the foundation for a historic performance in South Korea and Japan.
2004: Jamaica, semifinal round
Qualification wasn’t on the line, but with the Stars and Stripes in a group with the Reggae Boyz, an on-the-rise Panama side and El Salvador, a result was imperative as the US opened semifinal round play on the road at the notoriously difficult Independence Park.
A first-half header from Ian Goodison put the Jamaicans on track for a 1-0 victory and the US in an early hole thanks to El Salvador’s 2-1 win against Panama that same day. Luckily for the Americans, some late magic earned them a point and set the tone for the rest of group play.
In the 89th minute, Cobi Jones burst down the right flank, his cross eventually finding the feet of Landon Donovan. The young star found San Jose Earthquakes teammate Brian Ching wide open to smash home the equalizer and allow the US to leave Jamaica with a point and plenty of momentum.
The United States went on to finish the group undefeated, qualifying with a game to spare thanks to a 6-0 demolition of Panama at RFK Stadium.