1989 brought with it a new competition for the Caribbean Football Union, and the Antiguans, fresh off their OECS win the year prior, were eager to keep winning. The CFU Championship was no more, replaced by the Caribbean Cup: a bigger, more prestigious competition that gave the winner a berth for the CONCACAF Gold Cup. That tournament, then, offered the top two finishers qualification to the World Cup!

This gave the island nations of CONCACAF a much easier route to the international stage.

Sponsored by Shell, the final tournament was to be held in Barbados; the title sponsor was based there and the island had an international airport. The tournament consisted of a qualification group stage and a finals group stage, with the winners of both finals groups meeting in the championship final. Qualifications consisted of three groups, and the Benna Boys were placed in Group C.

The group stage was formatted where the winners of each group, plus the best two runners up, plus the hosting Barbuda, would qualify for the finals.

The tournament began for the Antiguans on April 23, 1989, with a fixture against regional powerhouse Jamaica. Luckily, Antigua was to play host, with the home field advantage St. Johns provided. Details are sparce, but we do know this: after only 22 minutes of play, Antigua led Jamaica 1-0, thanks to a goal by the legendary Everton Gonsalves. The Benna Boys kept the Jamaican side score less up to the final whistle. Yes, you read that right, Antigua managed to beat a team who had finished as high as 6th in CONCACAF play.

The Benna Boys kept the momentum going for their second fixture, to be played away in Dominica on May 13th. Again, not much is known, but again the Antiguans triumphed! 1-0 after 90 minutes! Antigua was leading the group!

Antigua and Barbuda had two remaining fixtures in group play: home against St. Lucia on May 21st, and away against Guadaloupe at some point that June. Unfortunately, records from Caribbean soccer are sparce, and not only do we not have scores for these two events, but we don’t even know when the second one was played. We do know that Guadaloupe won the group with 3 wins and a loss, and Antigua finished second with the same record. It came down to the unknown goal differential.

Grenada took Group A with 3 wins and 1 draw, while Saint Vincent and the Grenadines took group B with the same record.

The second placed teams consisted of three teams with identical 3 win, 1 loss records, with the two advancing decided on goal differential. Trinidad and Tobago finished second in Group A with a +14 goal differential, while Netherlands Antilles finished second in Group B with a +6 goal differential. Antigua’s goal differential isn’t known, but it was the lowest of the three, meaning that despite winning 3 of their matches, the Benna Boys would fail to qualify for the finals. Eventually, Trinidad and Tobago beat Grenada 2-1 to win it, but that’s not what we’re here for.

One of these days I really want to go to the CFU archives and dig through and see if I can’t find some of this missing data. It’s been an unfortunately recurring theme. I don’t know if it’s poor record keeping or a lack of tournament prestige or what, but there’s quite a lot of information missing that I’d love to have.

Anyway, with the disappointing loss on tiebreakers, the Antiguans were done for 1989. But, 1990 brought with it a new decade and another edition of the Caribbean Cup.

For the 1990 tournament, Antigua and Barbuda were placed in Zone C for qualification, one of four groups consisting of four teams each. The winner of each group would advance; no more second place tiebreaker nonsense.

Their competition began on April 14th, playing away on the island of Bermuda.

Six minutes in, the local boys went up 1-0 over the Benna Boys off a Sheridan Ming goal. Two minutes later, Antigua equalized, courtesy of Dion Greenaway. The half ended level at one goal a piece.

Two minutes into the second half, the one and only Everton Gonsalves worked his magic once again to give his country the lead for the first time. For thirty long minutes, the scoreline remained 2-1 in favor of the visitors, but in the 77th minute, Bermudan Corey Hill equalized. Antigua were unable to capitalize on the remaining 13 minutes, and the match ended, 2-2. Still, not a bad result at all.

Their second match was played away in Barbados, on April 29th. The first half saw no score, but 9 minutes into the second half, Adrian Hall put Barbados into the lead, one which they preserved. Antigua lost, 1-0.

Their final match was played at home a month later, hosting St. Lucia on May 27th. Earl Jean put the Lucians ahead in the 22nd minute, and added another in the 54th, to shut down Antigua and eliminate them from the tournament. For the second year in a row, Antigua finished second in it’s group.

Consistent as it may be, it meant for another year, no finals appearance. Fortunately for the Antiguans, though, they managed to make it to the OECS final in their smaller regional tournament, and on November 9th, they narrowly edged out Dominica at home, winning the tournament for the second time with a final score 2-1.

That was it for the Benna Boys until 1992. But more on that later.