Only once has Jamaica qualified for the World Cup, but the Caribbean island will likely never get a better chance to do so than the upcoming inter-confederation play-offs. 

The Jamaicans, under then-first-team coach Steve McClaren, have already spurned one golden opportunity to book their first World Cup appearance since 1998 by failing to qualify from a group featuring Curacao, Bermuda and Trinidad and Tobago, with a 2-0 loss to minnows Curacao proving costly. 

Still, Jamaica had a chance to make up for that defeat if they could only defeat Curacao at home in the final fixture of the group. Curacao instead held out for a 0-0 draw to book a fairytale appearance at the World Cup and prompt McClaren to quit as Jamaica boss. 

Now, with interim head coach Rudolph Speid at the helm, Jamaica faces an even more unlikely World Cup candidate in New Caledonia, a side ranked 150th in the latest FIFA World Rankings who only qualified for the upcoming play-offs by virtue of losing 3-0 to New Zealand in the final stage of the Oceania qualifiers. 

Boasting a squad full of MLS and English Championship players, along with a number of Premier League representatives, Jamaica should have too much against a team that would be the biggest underdog story in World Cup history. 

A victory against New Caledonia on March 26 is only half the battle, however. A date against DR Congo awaits Jamaica five days later, should they come through the play-off semi-final. 

The African side finished second in its qualifying group behind Senegal, collecting an impressive 22 points from 10 qualifying games and finishing just two points off automatic qualification after blowing a two-goal lead against Senegal at home. 

DR Congo, however, will be without Newcastle United striker Yoane Wissa, who is recovering from a lengthy knee injury, although they will have Real Betis winger Cédric Bakumbu and Spartak Moscow winger Théo Bongonda at their disposal. 

Still, the play-offs represent a chance at World Cup qualification that Jamaica has not tasted since 1998. They have not so much as made a World Cup play-off in the past 28 years and are likely to face much bigger obstacles for future tournaments, given that the US, Canada, and Mexico will also be competing in qualifying.

For more on Jamaica and the 2026 World Cup play-off, visit AMNY.com