England suffered relegation to League B in the Nations League after a 1-0 defeat to Italy at San Siro, a result which also equalled their worst run of form in eight years.
Giacomo Raspadori curled home the only meaningful attempt of the game for the hosts, capitalising on sloppy defending from Kyle Walker, who provided too much space for the Napoli man.
Italy's win was only their third in 10 matches, though the performance did little to ease concerns around Roberto Mancini's side.
It is England who face more immediate problems, though, with just 90 minutes of football left before the World Cup begins, and Gareth Southgate's men looked far from ready here.
A lacklustre first half saw both sides crippled by an inability to create any sort of threat in the final third, with neither Nick Pope nor Gianluigi Donnarumma called into action as play was limited to scrappy exchanges in midfield.
The early exchanges of the second half did not change much but Italy took the lead with their first meaningful chance of note, Raspadori collecting Leonardo Bonucci's long pump forward and given time to turn, before curling into the far corner beyond Pope's reach.
England's introduction of Jack Grealish and Luke Shaw after conceding, which finally gave the Three Lions a natural left-sided defender having started Bukayo Saka out of position, did not change the pattern of the game.
Harry Kane saw two shots saved by Donnarumma, though neither was particularly threatening, with Italy looking the more likely to extend their lead as Federico Dimarco struck the frame of the goal.
Jude Bellingham headed a late chance over the bar deep into stoppage time as England's fate was sealed on the final whistle.
What does it mean? World Cup worries for England
The mid-season fall of the World Cup in Qatar means no pre-tournament friendlies for the teams competing, giving England just 90 minutes of football before the opening group game against Iran, who beat Uruguay 1-0 earlier on Friday in a friendly.
Now five games without a win and 495 minutes without a goal from open play, Southgate is under intense scrutiny and his team selection continues to baffle – Saka starting at left wing-back, far from his natural position on the right wing.
While a lack of goals will always be concerning, the inability to even create opportunities despite an array of attacking options is a problem without an easy fix.
Raspadori's return
Raspadori's winning strike against England was his fourth in an Italy shirt since making his debut in June 2021, level with Nicolo Barella and with no player within Roberto Mancini's squad having scored more.
Italy's absence from the World Cup remains a bitter pill to swallow but Raspadori is already showing he can be a key player in the defence of the European Championship title in 2024.
Southgate's sorrows compounded
England's woes against Italy in front of goal were not a new occasion, the Three Lions having failed to score from open play in five games in the Nations League, having only scored from the penalty spot – an unwanted record they share with minnows San Marino.
With just 56 days before the World Cup, Southgate received boos from the travelling contingent at San Siro and requires a massive upturn in form if England are to equal their exploits in last year's European Championship.
What's next?
England's Nations League campaign comes to a close against Germany at Wembley on Monday, where Italy will face Hungary to decide the group winner.