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.
Fiorentina 2-2 Napoli: Kvaratskhelia keeps visitors' slim European hopes alive
Dethroned Italian champions Napoli's hopes of playing European football next season are hanging by a thread after they played out a 2-2 draw at Fiorentina in Serie A on Friday.
Napoli took the lead in the eighth minute through defender Amir Rrahmani, who nodded home a corner by Matteo Politano.
Cristiano Biraghi levelled for Fiorentina in the 40th minute from a free-kick, before M'Bala Nzola put the hosts in front two minutes later when he fired a shot into the bottom corner of the net.
Napoli's Khvicha Kvaratskhelia responded with another stunning free-kick early in the second half to rescue a point for his team.
Eighth-placed Fiorentina, on 54 points and with a game in hand, are five points behind Lazio in seventh.
They can still earn a Europa League spot either by leapfrogging the Rome side or by winning the Europa Conference League final in which they face Greece's Olympiakos on May 29.
Ninth-placed Napoli, on 52 points, still have a slim chance of making the Europa Conference League playoffs.
Data Debrief
Fiorentina left-back Biraghi has now scored six goals from direct free-kicks since the start of 2021-22, which is behind only James Ward-Prowse (seven) - now of West Ham and formerly of Southampton - as the most across Europe's top five leagues in that period.
Kvaratskhelia also levelled via a direct free-kick, making this the first Serie A match in which both teams scored via that route since Fiorentina against Lazio in April 2018 (Jordan Veretout and Luis Alberto in that case).
Southampton 3-1 West Brom (3-1 agg): Saints set up play-off final with Leeds United
Southampton saw off West Brom 3-1 at St Mary's on Friday to set up a Championship play-off final showdown with Leeds United.
Leeds thumped Norwich City 4-0 at Elland Road 24 hours earlier to book their place at Wembley, where Southampton now await on May 26.
The first leg between the Saints and West Brom finished goalless - just like the other semi-final - but the home side's quality told in the end.
Russell Martin's side dominated the first-half possession, with David Brooks going closest to scoring with a shot that hit the outside of the post.
Southampton made the breakthrough via a powerful Will Smallbone finish four minutes into the second half after Gray Diangana lost possession.
Darnell Furlong had a shot helped over by Alex McCarthy, while David Brooks - who assisted the opener - had a strong penalty appeal rejected.
Southampton remained in control, though, and Adam Armstrong scored a second with a shot through Furlong's legs and past Alex Palmer.
Armstrong's second goal arrived from the penalty spot in the 86th minute after Tom Fellows fouled Ryan Manning in the box, rendering Cedric Kipre's late header a mere consolation.
Marc Skinner signs Manchester United Women contract extension
Marc Skinner has signed a one-year contract extension as Manchester United Women head coach with the option of a further 12 months.
The 41-year-old guided United to their first major silverware last weekend with victory over Tottenham in the Women's FA Cup final.
United are fifth in the Women's Super League with one game to go - a massive drop on last term's runners-up finish - but Skinner will stay on.
"It's an honour to extend my stay at Manchester United," Skinner, who was appointed in 2021, told United's official website after the news was confirmed on Friday.
"I've always felt at home here, with our excellent players, staff, and fans.
"Being able to secure the team's first major trophy at Wembley was a real career highlight for me and another sign of our continued growth, on and off the field."
United conclude their campaign on Saturday against Chelsea, who lead Manchester City on goal difference entering the final day.
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