England added another chapter to their history of World Cup heartbreak in Saturday’s quarter-final against France.
But what were England’s most painful major tournament defeats, and does Harry Kane’s penalty miss even make it into the top five?
5. Argentina 1998
Michael Owen’s dazzling goal, David Beckham’s red card, Diego Simeone’s machiavellian antics, Sol Campbell’s would-be winner disallowed for spurious reasons: this World Cup second-round match had more drama than some entire England campaigns before inevitably ending with penalty woe.
4. Argentina 1986
It’s hard to top the Hand of God as a moment of English footballing injustice and this World Cup quarter-final would rank higher in the list had Diego Maradona not mitigated the impact of his moment of mischief with one of the all-time great goals a few moments later to send Bobby Robson’s team home.
3. Italy 2021
It all looked set up for Gareth Southgate’s likeable team to finally end 60 years of hurt when they swept to the Wembley final of last summer’s Covid-delayed Euro 2020 and took an early lead against Italy, only for the match to slip from their grasp and end in the familiar heartache of a penalty shootout defeat.
2. West Germany 1990
The match that began England’s penalty curse. Having ridden their luck to the last four, a Paul Gascoigne-inspired side gave as good as they got from a formidable West Germany team and really ought to have won before a titanic battle went to extra-time and the dreaded spot-kicks, with infamous results.
1. Germany 1996
England came within a Gazza toe of reaching the final of Euro 96, where they were hosts and football was coming home until it wasn’t. This was an agonising semi-final of near misses and what ifs as history repeated itself and Gareth Southgate joined Chris Waddle in the penalty shootout hall of shame.