
From winning their first World Cup qualifier this year, to advancing from a CONCACAF group stage for the first time, the Cayman men’s national football team has written a new historic chapter as they look to add to their legacy next month.
The team is slated to extend their significant run of 2024, when they face Guadeloupe in November.
The Cayman men, who have been on a tear of late, were promoted to League B and advanced to the 2024-25 CONCACAF Nations League play-in where they will face Guadeloupe on 10 Nov. at home and then away on 18 Nov.
In accordance with CONCACAF’s regulations for the tournament, the play-in matchups are determined based on the group stage standings. Since Cayman finished as the best second-place team from League C, they are slated to play Guadeloupe, the best fifth-place team from League A.
After Cayman plays Guadeloupe home-and-away, the aggregate score winner will advance to the 2025 Gold Cup preliminary stage – which would mark the first time the senior men will participate at that level.
The last time the two teams met was in 2008, when Guadeloupe thrashed the Cayman Islands 7-1 in a CAC Games match.
However, the Caymanian men have been silencing their doubters as of late with their solid play, and their goal is nothing less than a victory over Guadeloupe.

‘We made history’
Cayman’s recent form in the eyes of many has surpassed one of the best stretches of football since 2019, when Ben Pugh led the team to four victories and two losses in that year’s Nations League tournament, with the team just missing a promotion on goal differential.
However, for Cayman’s head coach Joey Jap Tjong, times have changed and the best is yet to come.
“We made history,” Jap Tjong said, after he led Cayman to advance for the first time from a CONCACAF group stage and earn a promotion to League B.
“We have shown our level and that’s the beginning because we can reach much more with these players we have.”
Looking back at St. Kitts drama
Within the last year, the Cayman team has notched wins against the US Virgin Islands, Antigua and Barbuda and the British Virgin Islands and came achingly close to beating St. Kitts and Nevis on Tuesday, 15 Oct.
With just seconds left on the clock and Cayman closing in on a monumental victory, a mistake resulting in an own goal cost the nation three points in the Nations League.
Controversy continues for Cayman and St. Kitts in a dramatic draw
Alfredo Whittaker, president of the Cayman Islands Football Association, was furious after the match and told the Compass biased officiating in favour of the St. Kitts squad ultimately led to the own goal.
“Unfortunately for us, we went down, and we equalised with an extreme amount of added time, which was initially nine minutes and went on to 11,” Whittaker said.
In the end, the Cayman senior men drew one-all with St. Kitts., at the Newtown Football Stadium, in their second-leg fixture. Cayman held off their tough opposition throughout the match, and took the lead in the 60th minute after Zachary Scott found the back of the net.
From that point on, the Cayman men kept their defence locked with commendable efforts, and even though the match official tallied up nine minutes of added time, Cayman, with the odds seemingly stacked against them, still clung tightly onto hope of a win and getting redemption from their 1-4 loss last month.
However, that hope was crushed after a deflection off Joshewa Campbell went into his own net.
“[The officials] were favouring the St. Kitts team,” Whittaker claimed. “They allowed them three offside goals in Cayman and now they gave them 11 minutes of added time at home.”
BVI beating
Prior to the St. Kitts draw, Cayman defeated the British Virgin Islands twice. The first win came at home on, 4 Sept., where Cayman beat BVI 1-0 after a perfectly placed goal by Elijah Seymour in the 84th minute.
Seymour noted to the Compass after the game that the team had a good mix of young and experienced players who share the goal of wanting to win.
And they would go on to win again against BVI in their second-leg fixture on 12 Oct., by the same 1-0 score, with Dimetri Douglas, who was subbed in, the hero this time, scoring in the 69th minute, seconds after entering the pitch.
“It means a lot to me to just come on and score on [my] first touch of the game,” Douglas said. “I was just thankful that I scored the winning goal.”
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