What if England Had Won the Penalty Shootout in 1990?

The ball is placed on the spot, the air thick with tension in Turin. Chris Waddle strides forward, hair mullet-perfect under the floodlights, a nation’s hopes humming in the silence. In reality, he blazed over and West Germany marched on. But what if Waddle had tucked his penalty past Bodo Illgner, if England had outlasted the Germans and reached their first World Cup final since 1966?

The ripple effect would have been seismic.

Sir Bobby Robson had already agreed to leave for PSV Eindhoven, his England tenure tainted by years of criticism. A final - and potentially a World Cup win - might have transformed his legacy entirely. Instead of being remembered as the nearly man who stumbled into redemption late in his reign, he could have returned home a national icon, forcing the FA to beg him to stay. His tactical flexibility, the way he unshackled Gascoigne and trusted Lineker, might have become the blueprint for the 90s rather than the cautionary tale.

Paul Gascoigne’s tears were the defining image of Italia ‘90. Booked and ruled out of the final, his story was one of heartbreak, of raw humanity. Had England won the shootout, Gazza would have missed the grandest stage - yet perhaps that would have spared him the endless reruns of his weeping face, the myth that both elevated and crushed him. Without the tragic iconography, would Gascoigne’s career have burned longer, steadier, rather than brighter and shorter?

Victory in Turin would have meant a date with Argentina in Rome. Maradona at half-pace, Claudio Caniggia suspended, a creaking team held together by grit and guile. England, buoyed by belief and powered by Lineker’s finishing, might well have beaten them. Imagine Bryan Robson lifting the World Cup alongside a tear-streaked squad, ending 24 years of yearning.

The cultural consequences are just as tantalising. Italia ‘90, even in defeat, reshaped English football: New Order’s “World in Motion,” Nessun Dorma, and the birth of the modern England fan experience. Yet winning the tournament would have supercharged it. The Premier League’s arrival in 1992 was already a revolution, but what if it had launched in the afterglow of England as world champions? The influx of foreign talent might still have come, but perhaps English players - Parker, Platt, Pearce, Gascoigne - would have been afforded a gravitas usually reserved for imported stars.

And what of 1996? That golden summer of “Football’s Coming Home” was fuelled by nostalgia for 1966 and the pain of repeated failures. Had England conquered in 1990, the mythos shifts. Euro ‘96 might have been viewed as the moment of empire defended, not empire dreamed. Penalty shootouts would not be a national trauma, but a test we had already passed. Perhaps Gareth Southgate never shoulders his infamous miss, his destiny altered by a country no longer haunted.

Of course, the Waddle miss is part of English football’s great narrative. The despair, the songs, the gallows humour – all forged in nights like Turin. A victory might have rewritten the story, but perhaps it would have stripped away some of the bittersweet beauty too.

Football thrives on what-ifs, and England’s 1990 heartbreak remains one of the richest. But it’s tantalising to picture Lineker lifting the trophy under Roman skies, Italia ‘90 remembered not for tears and trauma, but as the summer when England finally came home again.