Sombreros, Coin Tosses and Crossbar Heartbreak: How Football Invented the Penalty Shootout

Before penalty shootouts existed, football had some truly absurd ways of deciding knockout matches. We are talking coin tosses, drawing lots from novelty hats, and the occasional "let's just play again in two days" approach. It was chaos, frankly, and it took an Israeli referee and a pre-season English cup competition to sort it all out.

The Problem Nobody Wanted to Talk About

The 1968 Olympics quarter-final between Israel and Bulgaria ended 1-1. To settle matters, Israel's captain Mordechai Spiegler was asked to pull a piece of paper from a sombrero. Yes, a sombrero. He drew "no," and Israel went home. That same year, Italy reached the European Championship final after beating the Soviet Union via a coin toss following a goalless draw. They went on to win the whole thing, beating Yugoslavia 2-0 in a replay after the first final also ended level.

If you think VAR controversies are bad, imagine losing a major tournament because someone flipped a coin.

Enter Yosef Dagan

Israeli FA official Yosef Dagan, still fuming about the sombrero incident, teamed up with colleague Michael Almog to devise a better solution. Their proposal for penalty shootouts landed on FIFA's desk on 24 July 1969 and was published in FIFA News the following month. By 27 June 1970, IFAB had formally adopted the idea at its AGM in Inverness. Football would never be the same.

The Night It All Began

On 5 August 1970, a crowd of 34,007 packed into Boothferry Park, Hull, for a Watney Cup semi-final between Hull City and Manchester United. Chris Chilton gave Hull the lead on 11 minutes, Denis Law equalised in the 78th, and after extra time settled nothing, football history was about to be written.

What happened next is widely cited as the first professional penalty shootout in England, though FIFA itself has no records confirming whether it was truly the world's first. Either way, nobody at Boothferry Park that night had a clue what they were doing.

George Best, ever the trailblazer, stepped up and became the first player to score in a shootout. Denis Law, his illustrious teammate, then became the first to have one saved, with Hull keeper Ian McKechnie keeping it out. McKechnie's moment of glory was short-lived, however. When it came to his turn to take a penalty (goalkeepers took them too, because why not add to the madness), he clattered the crossbar. Manchester United won 4-3 on penalties. McKechnie held the unique distinction of being both the first keeper to save a shootout penalty and the first to miss one.

A Legacy of Agony and Ecstasy

The penalty shootout quickly became football's most dramatic device. The 1976 European Championship final saw Czechoslovakia beat West Germany, with Antonin Panenka delivering his now-famous chipped penalty. Three World Cup finals have been decided on penalties: 1994, 2006 and 2022. And England's men? They have lost seven shootouts at major tournaments, a statistic that requires no further comment.

Research suggests roughly one in four penalties in shootouts are missed or saved, meaning the format delivers heartbreak with reliable efficiency.

The FA Cup did not adopt shootouts until the 1991-92 season, prompted by the farcical 1990-91 fourth-round tie between Arsenal and Leeds United that required three replays to produce a winner. Some traditions die harder than others.

Just days ago, Wales saw their 2026 World Cup dreams ended by Bosnia-Herzegovina in a penalty shootout, proving that Dagan's invention remains as ruthlessly effective as ever. Whether you love them or loathe them, they are a sight better than pulling scraps of paper from a sombrero.

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