Roy Hodgson's side crashed out of Euro 2012 losing 4-2 on penalties to Italy as another tournament ended in spot-kick heartache for the Auld Enemy.
A quarter-final berth would have been regarded as a success for the England boss and his squad as they left for Poland and Ukraine a fortnight ago but, despite topping their section ahead of France, the Three Lions never really looked capable of making the last four.
It is Cesare Prandelli's side who booked their place in the semi-finals, joining Spain, Germany and Portugal, moving them one step closer to another major trophy as they prepare for a meeting with Joachim Low's side.
A shoot-out defeat may open old wounds for England but they deserved little on the night, with the Azzurri in control throughout as only their profligacy stopped them winning the match in a scoreless 90 minutes.
The Kiev tie had been billed as a battle of tactical nous as two cautious coaches pitted their wits against each other but from the off there seemed little chance of the last-eight fixture being a war of attrition.
After just three minutes, Daniele De Rossi had English hearts skipping a beat as a superb, curling, dipping effort from long range saw Joe Hart scrambling across his goal as the ball rattled his right-hand post. Seconds later, it was his opposite number, Gianluigi Buffon who was called into action, saving a tame effort from Glen Johnson.
Having seen Wayne Rooney mark his maiden appearance at these finals with the decisive goal in their final Group D match with Ukraine, the hopes of the nation were again pinned on the Manchester United forward delivering on the big stage. It was the star from the blue half of the city however, who would pose the biggest threat in front of goal.
As the whistle blew on an intriguing first 45 minutes, the Italians could have had one foot in the semi-finals, courtesy of Mario Balotelli. The Azzurri forward is often a derided figure but he appeared in the mood to silence his critics on one of the biggest nights of his fledgling and controversial career.
He was frustrated in front of goal, however. On 24 minutes, he plucked a terrific floated pass from Andrea Pirlo out of the Kiev sky but was foiled by John Terry before he could test Hart. His Eastlands compatriot denied him moments later but his best chance was still to come as the 21-year-old failed to convert when just yards out after meeting Antonio Di Natale's cushioned header.
England's frail defensive line was being exposed at regular intervals, with theThree Lions hanging on as the Italians turned on the style. Hodgson prides himself on making his side resolute and hard to break down, but the Azzurri had Hart's goal under siege as the match ticked on, with Pirlo the midfield mastermind controlling proceedings as he patrolled the middle of the park.
It was De Rossi who would spurn the most glaring opportunity, dragging his effort wide of target from close range after Claudio Marchisio's header caught England sleeping.
Just a few minutes later, Riccardo Montolivo got in on the act, firing over from six yards after Balotelli was again foiled.
By the time Hodgson's men got within striking range of an untested Buffon, it was too late to force an unexpected winner, with an off-target acrobatic effort from the frustrated Rooney the total of their attacking intentions in the second half.
The period of extra time didn't give England more time in which to book a semi-final berth, but just another 30 minutes in which to hang on and battle against wave after wave of blue attacks.
Alessandro Diamanti almost broke the deadlock in fortuitous fashion, seeing his cross hit Hart's post before Antonio Nocerino's header was ruled out for offside.
And so it was to penalties.
After Balotelli and Gerrard slotted home, Italy blinked first as Montolivo fired wide before Rooney hammered home England's advantage.
It didn't last long. Pirlo topped off a sublime display as he showed nerves of steel to dink the ball down the middle. It was a trick Ashley Young couldn't repeat, smashing his effort off Buffon's bar before Nocerino netted.
It was left to the Juventus keeper to emerge the Italian hero, saving a tame effort from Ashley Cole before Diamanti inflicted the final blow to England's Euro dream.