Marcus Rashford, Jadon Sancho and Bukayo Saka missed consecutive spot-kicks as the Azzurri won 3-2 after the 90 minutes finished with a 1-1 draw.
Given his own history in this competition, it was a cruel twist that the two players Gareth Southgate introduced for penalties – Rahsford and Saka – both missed.
But Southgate and his players has ensured there will be no villains in this England squad, only heroes, and the manager will know better than anyone how to comfort his players.
It was a tragic end to the tournament for a coach and squad who have redefined expectations in the country and the image of the England national team around the world.
Going down on penalties was a familiar way to lose, of course, and Southgate will reflect that there was also evidence of old failings in his side’s performance, which suggests there are still steps to make if England are to replicate this run in Qatar in 18 months.
England’s journey through the Euros has been framed by their World Cup semi-final defeat three years ago, with the survivors from Croatia insisting that they have learned from that painful night in Moscow.
This game actually followed a remarkably similar pattern, with England scoring early but failing to hammer home their dominance, before inviting too much pressure and eventually conceding mid-way through the second half.
In fact, Leonardo Bonucci’s 67th-minute goal to cancel out Luke Shaw’s opener came at exactly the same point in the game as Croatia’s equaliser.
The question from there was whether England could change the record and really prove they are a different animal by turning the tide and wrestling back control of the match.
Ultimately, they could not, and Italy finished normal time as the more menacing of the two sides, even after Southgate had attempted to reassert England’s dominance with the introductions of Saka, Jordan Henderson and later Jack Grealish.
The manager has always dismissed the significance of history but he must have been frustrated by the way his players dropped too deep too early and failed to keep hold of the ball – just as England have done many times before in big knockout matches.
As against Croatia, England could not have dreamed of a better start when Shaw fired them ahead with the fastest-ever goal in a European Championship Final after one minute and 57 seconds.
The strike came from a combination of Southgate’s wing-backs, with Shaw converting Kieran Tippier’s cross at the back post, as the manager’s change of system befuddled Italy.
But the Italians soon earned a foothold and ultimately shaded a compelling, nerve-shredding affair before it came down to penalties.
These players deserve better than ugly scenes
Whatever the end result, the tournament has fostered the type of celebrations not seen in this country for a generation and there have been many uplifting scenes and moments.
The euphoria inside Wembley after the semi-final win over Denmark will long live in the memory and there was palpable pride at full-time here for Southgate and his players.
Once again, the Wembley crowd was magnificent on the night, spurred on by Shaw’s early goal and thereafter determined to lift England in difficult moments.
At half-time of extra-time, even in the most nail-biting conditions imaginable, the entire stadium roused itself to roar England to one last push.
If Russia rebuilt the connection between England and their fans, then this tournament has given the bond a permanence and redefined the attitude of England fans towards their team.
It feels like the very outlook of supporters has shifted. They no longer expect to be let down. Like Southgate’s players, supporters have adopted the manager’s calm belief.
And yet, on the most unforgettable occasion, there were elements the country would rather forget, as a sizeable minority of supporters were responsible for ugly scenes around the stadium and elsewhere.
Stewards were overrun as groups of alcohol-fuelled fans stormed the gates. Ticketless supporters made it inside the ground. Fights broke out.
There were reports of terrified children in tears – their happiest memory briefly turned into a nightmare – and widespread anti-social behaviour.
UEFA, the FA and police face uncomfortable questions about how it was allowed to happen, and it should not be overlooked as a one-off given the occasion.
The biggest difference between this England squad and previous generations, and what makes them so easy to love, is that they seem to represent the best of us and offer a picture of the country as many of us would like it to be: principled, unified, inclusive, morally-courageous, fearless, talented, proud.
There was a time when it was often said that England did not deserve such loyal support, such were their consistent shortcomings.
Now the narrative has shifted. These players deserve better than the supporters who stormed Wembley and sacked London.