England have failed to reach the semi-finals of the European Under-21 Championship for the third time in succession following a 3-1 defeat to Italy in their final Group B fixture.
Knowing that a victory would see them safely through to the final four, Gareth Southgate's side were stung by a quickfire double from Andrea Belotti and Marco Benassi midway through the first half.
The latter scored once again after the break to set the seal on an impressive performance that was not enough for the Azzurri to progress due to Sweden's draw with Portugal. Nathan Redmond notched a late consolation.
England started the evening brightly, maintaining a quick tempo that led to a flurry of early corners and the first real chance of the evening through new Liverpool recruit Danny Ings.
After receiving possession from Nathaniel Chalobah in midfield, Harry Kane sent a lovely through ball into the path of his strike partner. With only Francesco Bardi to beat, however, Ings totally lost composure and fired harmlessly wide.
Kane was next to try his luck, displaying a glorious first touch to bring down Carl Jenkinson's switched pass but his powerful shot was well parried.
Italy created little by way of clear-cut chances early on, but that quickly changed after 25 minutes when they grabbed the opening goal as Belotti took advantage of some notably slack defending to beat his stationary markers and turn Domenico Berardi's cross home on the stretch.
England did not respond adequately to going behind and within 90 seconds the deficit was doubled. Lorenzo Crisetig was awarded the freedom of the Andruv Stadion as he surged into the England half totally unchecked before passing to Benassi.
The Torino midfielder's low effort took a deflection off Ben Gibson that caught Jack Butland off guard and saw the ball nestle firmly in the bottom corner.
England were evidently shocked and much of their passing in the first half was neat but largely predictable and badly lacking in any real threat. They did fashion two chances before the interval, but Bardi reacted well to keep out efforts from Redmond and Kane.
Having proved his quality with an impressive winner during the 1-0 victory over Sweden on 21 June, Jesse Lingard started the second half with pleasing purpose.
The Manchester United winger combined well with Luke Garbutt down the left flank before bamboozling his marker with a fine burst of skill and shooting agonisingly wide.
Lingard proved himself to be arguably England's biggest threat as the match wore on, with a curled right-footed effort just evading Bardi's left-hand post.
Italy extended their lead further after 74 minutes as Benassi leapt highest to head in after Marcello Trotta had hopefully hooked a throw-in over his shoulder and into the penalty area.
Kane, having laboured in his attempts to replicate the blistering club form shown for Tottenham last season, took the initiative in an attempt to reduce the arrears but his midas touch was lacking as he sent a header wide before failing to hit the target from distance.
Ings then just missed out on a wicked low ball sent across the face of goal before Norwich winger Redmond provided a brief moment of cheer in stoppage time with a swerving effort that was set up by a fine flick from substitute Ruben Loftus-Cheek.