Some footballers are remembered for the trophies they lifted. Others for the clubs they graced, or the records they broke. But a few enter the realm of folklore for one reason alone: they dared to challenge a god—and won.
Ulysses. Hercules. Fast forward a few centuries, and we find Tomislav Ivković.
In an era when Diego Maradona walked the earth like a deity, with defenders and goalkeepers alike reduced to mere mortals, Ivković stood tall. Not once, but twice, he faced the Argentine maestro from the penalty spot. And twice, he denied him. He even had the gall to bet Maradona $100 he’d save his penalty.
This is the story of the man who made that bet. And won.
The Boy from Zagreb
Born on August 11, 1960, in Zagreb—then part of Yugoslavia—Tomislav Ivković came of age in a footballing culture obsessed with technical flair and tactical discipline. He was a product of Dinamo Zagreb’s youth system, one of the region’s most storied clubs, and made over 50 appearances before being sold in 1983 to rivals Red Star Belgrade following disagreements with his coach at the time, Miroslav Blažević (yes, the same Blažević who would later lead Croatia to third place in the 1998 World Cup).
But it was abroad that Ivković would truly make his name. After a few seasons in Austria, where he played for Tirol Innsbruck and Wiener SC, and a brief spell in Belgium with Genk, it was in Portugal where he would spend the bulk of his club career.
In the summer of 1989, Sporting Lisbon’s* recently elected president Sousa Cintra announced that he had signed one of Europe’s best goalkeepers. The club was still looking for someone to fill the void left by the iconic Vítor Damas. Tomislav Ivković was bought for €450,000 and would go on to be the club’s starter for the next four seasons, amassing 157 official appearances.
It was while at Sporting that he first faced Diego Armando Maradona.
The First Duel: Naples, 1989
September 27, 1989. Stadio San Paolo, Naples. Second leg of the first round of the UEFA Cup.
Napoli vs. Sporting Lisbon.
On one side, the future Italian champions, led by the brilliant Maradona, in his sixth of seven seasons at the club. Around him, Brazilian internationals Alemão and Careca, and Italian stars Andrea Carnevale, Ciro Ferrara, Gianfranco Zola, and Fernando De Napoli.
On the other side, a less memorable Sporting team whose main figures were:
- Fernando Gomes, a 33-year-old veteran and prolific goalscorer (twice winner of the European Golden Boot), signed from rivals Porto;
- Carlos Manuel, 32, the club’s captain and midfield leader;
- Oceano, a powerful midfielder who would later become one of Sporting’s most iconic captains.
- And in goal, 29-year-old Tomislav Ivković, in his first season at the club.
After a 0–0 draw in Lisbon, the second leg also ended 0–0. The tie would be decided on penalties.
There is footage on YouTube. Ivković walks off his line to speak to Maradona at the penalty spot. He later told the Portuguese press:
“When he was going to take his penalty, I approached him and said: ‘Do you want to bet $100 I’ll save it?’ He accepted.”
Maradona struck to the keeper’s left, but Ivković guessed correctly and saved with his left hand. And he didn’t wait. While Maradona was still standing with his hands covering his face, Ivković approached him and made sure he knew he had lost the bet.
Maradona was a man of his word.
“At the end of the game, Maradona gave me his shirt and the $100.”
Despite winning the bet, Sporting lost the shootout. “Il vecchio Gomes,” as the RAI Due commentator called the veteran striker, smashed his penalty against the bar.
Napoli themselves didn’t get far in the competition, losing 3–8 on aggregate in the third round to Werder Bremen, managed by Otto Rehhagel and featuring Karl-Heinz Riedle, Dieter Eilts, and Rune Bratseth.
But later that same season, Napoli won the Serie A. The second league title in their history.
“
When he was going to take his penalty, I approached him and said: ‘Do you want to bet $100 I’ll save it?’ He accepted.
The Pentapichichi Era
At Real Madrid, Sánchez became the focal point of one of football’s most elegant machines. He joined La Quinta del Buitre, the famed generation of homegrown stars—Emilio Butragueño, Míchel, Martín Vázquez, Sanchís, and Pardeza.
Together, they dominated Spanish football. Real Madrid won five consecutive league titles from 1985 to 1990, added the Copa del Rey in 1989, and lifted the UEFA Cup in 1986, defeating FC Köln 5–3 on aggregate.
Hugo Sánchez was their spearhead. A poacher, a showman, a predator of space. He won four straight Pichichi trophies during that run—and five in total. Hence the nickname: Hugol. Or, more fittingly, El Pentapichichi.
The Second Duel: Florence, 1990
June 30, 1990. Stadio Artemio Franchi, Florence. Quarter-finals of the World Cup.
Argentina vs. Yugoslavia.
On one side, the reigning world champions, led by a battered but still brilliant Maradona, flanked by Basualdo, Burruchaga, and the irrepressible Claudio Caniggia.
On the other, a talented Yugoslav side boasting Dragan Stojković, Robert Prosinečki, and Dejan Savićević (who came on in the second half, after sitting alongside fellow Yugoslav stars Darko Pančev, Alen Bokšić, Davor Šuker, Zlatko Kranjčar, and Robert Jarni on the bench). (Please verify full bench and subs list.)
After 120 minutes of a goalless stalemate, it went to penalties.
Maradona stepped up third for Argentina, after Serrizuela and Burruchaga had scored. He looked confident. But so did Ivković. Their previous encounter hung heavy in the air.
“When it came to the penalty shootout, it was all about psychology,” Ivković told FIFA TV.
“So I said to Maradona: ‘I know where the ball is going to go – I’m gonna save it and there is nothing you can do about it’ – he never looked at me, just kept his eyes on the ball. I pointed to my left—the side I saved last time. Then, just before he shot, I faked to the same side and dived the other way.”
Ivković guessed correctly. “He literally passed the ball to me,” he said.
It was seismic. Maradona, missing a penalty at a World Cup? Unthinkable.
Argentina eventually won the shootout thanks to Sergio Goycochea’s heroics. But Ivković had done the unthinkable. Twice. A goalkeeper who refused to be intimidated.
The footage is there. The newspapers wrote about it. The legend was born.
Who saves two penalties from Diego Maradona in the same season?
Tomislav Ivković does.
Not Just a Penalty Hero
Though the penalty saves became his myth, Ivković’s career deserves more than a footnote.
He earned 38 caps for Yugoslavia, debuting in 1983. He was selected for Euro 1984 (as second-choice behind Zoran Simović), won Olympic bronze in 1984, and was Yugoslavia’s first-choice goalkeeper at Italia ’90. In an era stacked with elite keepers—Pfaff, Zenga, Shilton—Ivković held his own.
At club level, he was Sporting’s trusted number one from 1989 to 1993. After a more irregular season, Bobby Robson let the 33-year-old leave. He continued in Portugal for Estoril, Vitória Setúbal, and Belenenses, had a brief spell in Spain with Salamanca, and closed his career at Estrela da Amadora, becoming one of the most recognisable foreign goalkeepers in Portuguese football history.
Unflashy, disciplined, with excellent reflexes and a flair for the dramatic, he was a keeper who relished the big stage.
Life After the Gloves
After retiring, Ivković ventured into coaching. He managed clubs in Croatia, Iran, and Saudi Arabia, and earned a reputation as a no-nonsense figure—outspoken, principled, emotionally invested in his teams.
Despite a colourful coaching career, he never quite escaped the shadow of those Maradona moments.
And maybe, he never wanted to.
He never played for Real Madrid. Never for Manchester United. Never lifted a Champions League trophy.
But when the best player in the world stepped up to beat him—twice—he didn’t blink.
The Keeper Who Laughed at a God
Football, at its most beautiful, is theatre. Heroes and villains. Scripts written by fate. And every so often, a moment that feels like myth.
Tomislav Ivković’s story is one of those myths.
He was the mortal who dared to bet against a god. The man who stood, twice, across from Diego Maradona—and refused to bow.
And in a sport ruled by glory and goals, he reminds us that sometimes, the most unforgettable act is a save.
* Yes, we know Sporting prefers to be called Sporting Clube de Portugal. But here, we find it romantic to revive the old ways. “Sporting Lisbon” feels like a chapter title from another era. And that’s exactly what Jay-Jay is about.
Valdo – provisory title
He dribbled like a dancer, played with a smile, and made chaos look beautiful. A rebel with the ball, and a genius no system could ever hold down.
Italy’s 90’s Goalkeepers – provisory title
He dribbled like a dancer, played with a smile, and made chaos look beautiful. A rebel with the ball, and a genius no system could ever hold down.
Emilio Butragueño – provisory title
He dribbled like a dancer, played with a smile, and made chaos look beautiful. A rebel with the ball, and a genius no system could ever hold down.
