116 teams entered the 1990 World Cup, including Italy as the host nation and Argentina as reigning World Cup champions, who were both granted automatic qualification. Thus, the remaining 22 finals places were divided among the continental confederations, with 114 initially entering the qualification competition.
Due to rejected entries and withdrawals, 103 teams eventually participated in the qualifying stages.
Thirteen places were contested by UEFA teams (Europe), two by CONMEBOL teams (South America), two by CAF teams (Africa), two by AFC teams (Asia), and two by CONCACAF teams (North and Central America and the Caribbean). The remaining place was decided by a play-off between a CONMEBOL team and a team from the OFC (Oceania).
Both Mexico and Chile were disqualified during the qualification process; the former for fielding an overage player in a prior youth tournament, the latter after goalkeeper Roberto Rojas faked injury from a firework thrown from the stands, which caused the match to be abandoned. Chile were also banned from the 1994 qualifiers for this offence.
Three teams made their debuts, as this was the first World Cup to feature Costa Rica and the Republic of Ireland, and the only one to date to feature the United Arab Emirates.
For Costa Rica it was like a dream come true.
They were pitted against Brazil, Sweden, and Scotland in Group C. Brazil were expected to qualify for the Round of 16 without any hassles whereas the competition for the second would be between Sweden and Scotland. Since 1974, Scotland had been a very tough contender in the World Cups, but they failed to live up to the expectations. Perhaps in Italy, they might break the jinx.
Among these teams, who boasted an enriched World Cup history, Costa Rica were simply no-hoppers.
On June 11, 1990 at Genoa, Costa Rica met Scotland.
The Scotts were expected to win without breaking enough sweat, but throughout the 90 minutes, they had to try hard to come back against the North American Nation.
In the 49th minute Juan Cayasso scored the decisive goal, which sealed the fate of the match.
The Costa Rican striker, Claudio Jara, had produced a stunning back-heel at the edge of the box to put the 28-year-old midfielder one-on-one with Scotland goalkeeper Jim Leighton. Cayasso dinked the ball over Leighton and scored the historic goal.
“I don’t know if I remember it because I always see it on video people play,” recalls Cayasso, speaking from his office in Limon on Costa Rica’s lush Caribbean coast where he directs grassroots sport. “But I could never be prepared for that moment. My teammate Claudio Jara, knocked the ball to me – we call it a taquito here. I was close to him, I step back and when he does the taquito I read it. At first, I’m like, ‘Oh…’ I’m frightened. But then I have to react, it’s at my foot, Jimmy is out. Then it hits his belly and goes over him. I turn around and look at the referee, and he’s going to the center of the field. First I’m frightened, then I don’t believe it, then, ‘Yes, goal.’ I had gone far away at that moment. My mind was all about Costa Rica,” said Cayasso in an interview published in The Herald.
The Scottish fans and press were shocked. They did have their flaws, but the credit should be given to Costa Rica for keeping their nerves until the end of the final whistle and bag full points.
Costa Rica were coached by the Yugoslavian Bora Milutinović, who had taken the job in February 1990. But the preparations were not up to the mark as the other teams in the group. Still, Bora instilled confidence among players and always backed them to fight and display mental strength.
“Bora had the experience from coaching Mexico in the World Cup, and he was like a father who knew about what we would have to go through. For him, we were playing so bad. I thought he thought we had not much chance before going to the World Cup. But he always kept so cool. And once we got there, I think he got a little bit more faith about what could happen. He was very important for us in terms of our mentalities” said Cayasso
“It was something incredible, very exciting, which stirred a whole set of feelings that are hard to describe and has represented many blessings over the years, like receiving the whole country’s affection,” Cayasso told EFE.
Costa Rica would lose against Brazil, but Luis Gabelo Conejo’s gallant goalkeeping overshadowed the Brazilian victory in Turin, where the shirts of Tico were designed like that of Juventus to earn support from the local crowd, who were mostly backing the Samba Boys.
In their last group match, Costa Rica beat Sweden despite trailing by 1-0. Flores and Medford scored in the 75th and 87th minutes respectively – Costa Rica would feature in the Round of 16 along with other Big Boys of world football.
“In the place where we were staying I was sitting in the corner thinking about what had just happened,” he says. “We had beaten Scotland and I was thinking was this true or not? I was in shock. Thinking about qualifying? No, no one was thinking that. We got confidence. Things came out good against Brazil and then we started thinking we have a chance. Scotland won 2-1 against Sweden, which was good for us because we beat Scotland,” said Cayasso.
“Some of us were like, ‘we qualified, we can go home now.’ And some of us were like, ‘No, we can stay more. We can win against Czechoslovakia. Then its [West] Germany in the next game.’ The mind of the team was out of synch.”
In the Round of 16, Czechoslovakia crushed them, but they would leave Italy with their heads high.
One might claim, in a tournament of shock, Costa Rica’s progress was just another fluke.
But Cayasso differs with such an opinion.
“We had some very important things happen. We had a lot of friendly games against European teams. We qualified for the Olympic Games in Moscow [1980} and then the Los Angeles  Games. That generation of players went to those, getting a lot of experience.”
“In 1990, Alajuelense and Saprissa [Costa Rica’s biggest club sides] had Czech trainers, European trainers. So we had that European mentality to play the way they play because the football in Costa Rica was so slow. It was the right moment.”
As part of their preparations to play Scotland, Costa Rica played an international friendly against Wales in Cardiff.
They lost by 1-0, but it helped them to get an idea about the British-style-of-play.
Conejo had a bad day and the Scottish scouts reported to the manager that he was a weakness.
But this information proved wrong as Conejo had a great tournament until things fell apart against the Czechs.
“It’s true, when Gabelo was in Costa Rica, he played with a very small team, always losing by three, four or five. It was so bad. That’s why I think it was a miracle: Gabelo was the best one of us,” Cayasso says.
“I wrote a book called The Goal from Italia 90: Destiny, Luck or Chance. It was so crazy. We planned so many things against Scotland, to play the tactical way, on the outside, but no one went on the outside. We see Gabelo coming out and holding high balls against big players. I don’t know how they didn’t score against us. Gabelo was incredible but that wasn’t so normal.”
Costa Rica impressed all in the World Cup 2014, but Italia 90 had been the one, which gave Costa Rican football the much-needed push.
While, that afternoon at Genoa on June 11, 1990, would always remain as the red letter day for Costa Rica and Cayasso.