We last ended in 1986, with the Benna Boys bowing out of Central American and Caribbean Games qualifying after two matches.

1987 brought with it a brief foray into Olympic qualifying, with a pair of draws against the Dominican Republic. Despite neither side winning, the away goals rule took effect, with the Dominican Republic scoring their only goal during the leg hosted in Antigua. An unfortunately early exit from the tournament, and with that, the end of international competition for Antigua in 1987.

However, 1988 was set to be the busiest year yet for the Benna Boys.

March of 1988 brought with it another round of CFU Championship qualifying.

For the home and away series, Antigua would be facing their most recent victims, Dominica, who, despite taking an early lead with an 18th minute goal from Robert Hippolyte, wound up level at half time thanks to a late goal from Steve Hurst, and had their fate sealed with yet another goal at the increasingly legendary feet of Everton Gonsalves in the second half. That win back in 1985 put Antigua through to the next round of qualification, but eventually lost 1-0 to Guadeloupe.

After three years, Dominica was out for revenge, and Antigua was hoping to go two-for-two.

The first match, played away in Dominica, was a relatively tame affair, with the hosts managing to hold the visiting Antiguans to a scoreless draw. The same, however, can’t be said for the leg hosted in Saint John’s.

The match started out rough, with Dominica conceding a penalty in just the 18th minute. Everton Gonsalves made swift work of it, and put the home town favorites up 1-0. Late into the first half, the visiting Dominicans own McIntyre equalized with a goal in the 44th minute.

The teams entered the second half still level, but in the 70th minute, Antiguan player Anthony scored the go-ahead and eventually game winning goal in the first Antiguan victory in over three years.

The Benna Boys were through to the next round.

The CFU Championship finals were scheduled for July of 1988, but before that, another tournament: the CONCACAF Championship, which counted for 1990 World Cup Qualification!

For only the third time in their brief history, Antigua and Barbuda would be fighting it out on the biggest international stage of all! Or, at least, that’s what they planned. But before that, they must qualify.

The two tournaments would overlap, with one qualifying match hosted against Curacao, followed by the three matches of the CFU Championship finals, then the second qualification leg, and then Olympic qualification for the 1988 Summer Games. A very busy summer for the Antiguans.

The Benna Boys had a less than ideal start to the summer, dropping the first qualifying match 1-0 at home against Curacao. Hoping to put this loss behind them, the Antiguans traveled to Martinique for the 1988 CFU Championship Finals. Their first of three matches was against the host nation.

The start of the Finals competition was a high scoring affair, and at the final whistle, Antigua remained level against Martinique with a score of 2-2. The second match, played just two days later, saw Antigua draw long standing rivals Trinidad and Tobago 1-1. Another two days after that saw the Benna Boys conclude the Finals with a third consecutive draw, this time 0-0 against Guadeloupe.

Despite failing to win any of their three matches, Antigua and Barbuda’s three points from three draws was good for second place, behind eventual second time champions Trinidad and Tobago. While it might not seem like much, this was the best finish ever by Antigua in any international tournament. They had only made the finals twice before, and finished last both times.

Hoping to carry this momentum through to their second CONCACAF/World Cup qualification match against Curacao, the Benna Boys traveled to the Netherlands Antilles for what proved to be a much tougher task.

Antigua wound up scoring their only goal as of yet in the tournament, going level at 1-1 in aggregate, but in extra time, eventually conceded three goals, losing 4-1 overall. Not the outcome they hoped for, but after the incredibly busy summer, was still not that bad a result.

Plus, it set up the Benna Boys for something unprecedented.

But first! Some history!

In 1981, the Organization of Eastern Caribbean States was founded with the Treaty of Basseterre. This succeeded the previous West Indies Associated States, a union of islands whose status changed from British colonies to semi-dependent states maintaining association with the United Kingdom in 1967. Due to many of these nations declaring independence, the union became obsolete, leading to the foundation of the OECS.

This organization hosted a soccer tournament in the fall 1988, and Antigua and Barbuda made the final.

This time, instead of a round-robin bracket, there would be a more traditional championship match.

On November 20, 1988, Antigua hosted Saint Lucia for the OECS final, and in front of the home crowd, scored two unanswered goals and won their first ever international championship!

Yes, the Benna Boys finally did it. And while the OECS title might not be as impressive as many other competitions, it’s still a major international victory.

The remaining month of 1988 didn’t see any international play for the Antiguans, but it did see the creation of an new Caribbean championship tournament. The CFU Championship would be folded into the new Caribbean Cup, with the inaugural tournament to be held the following year in Barbados. This would feature three groups and sixteen teams, more participants than any prior Caribbean tournament.

And Antigua was entered.