England suffered the embarrassment of relegation from their Uefa Nations League group after slumping to defeat against Italy in Milan.
Giacomo Raspadori's stunning 68th-minute strike broke the deadlock in the San Siro as a game that lacked any spark finally came to life after the break, with England's winless streak extended to five games, their worst since June 2014.
Raspadori produced instant control and a fierce right-foot finish which gave goalkeeper Nick Pope, in for the injured Jordan Pickford, no chance.
Manager Gareth Southgate kept faith with Harry Maguire despite his struggles at Manchester United, the defender suffering one anxious early moment when West Ham United striker Gianluca Scammaca beat him in the air at the far post, only for a combination of Pope and the woodwork to keep his header out.
England responded at last, Italy keeper Gianluigi Donnarumma producing a fine double block from Harry Kane, although the home side had chances of their own in a frenetic finale.
Southgate was keen to refocus after their run without a win put them in trouble in their Uefa Nations League group but there was little to get excited about here as the latest goalless show left them 495 minutes without a goal in open play.
Kane threatened Donnarumma as England tried to react but there were barely any other clear-cut chances, despite the promptings of Phil Foden, apart from a late Jude Bellingham header that he sent over the bar.
Arsenal's Bukayo Saka had been named as England's player of the year before the game and his reward was a role in an unfamiliar left-wing back position in which he made little impact, perhaps understandably, before he was substituted.
It was hard not to feel sympathy for the youngster being asked to perform such an unaccustomed role at this level.
Maguire had few serious alarms but England did not deserve anything from the game and must now raise themselves against Germany at Wembley on Monday with their Uefa Nations League fate already decided.
And Southgate must surely involve Brentford's Ivan Toney, surprisingly excluded from the match day squad here. Anything else would make a nonsense of his call-up.
This was another disappointing night for England which did nothing to lift the spirits after their recent poor run.
Southgate must raise confidence
England must pull themselves out of this ill-timed slump with only 90 minutes of international football left before the World Cup starts in Qatar in November.
Time is running out with the showpiece drawing closer and England hitting their worst run of form since 2014, making a mockery of their elevated status as one of the World Cup favourites.
Relegation now means they drop out of the elite groups of the Uefa Nations League and could face a potentially harder draw in the next Euros.
England had formed a habit of getting the job done even when not at their best but this has been lost now and the lack of potency, thus leaving an even greater reliance on Kane, is a real concern for Southgate.
He will have hoped to have his World Cup thoughts crystallised by now but England's current mediocre form is raising more questions than answers.
BDST: 1400 HRS, SEP 24, 2022