Bengaluru, September 24: England suffered relegation to League B in the UEFA Nations League after a 0-1 loss to Italy at the San Siro Stadium in Milan a result which also equalled their worst run of form in eight years, while Hungary edged Germany 1-0 in Leipzig
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 and 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.
Meanwhile, Adam Szalai's sublime finish kept Hungary on course for the Nations League Finals as they beat Germany 1-0 in Leipzig.
Captain Szalai struck almost midway through the first half on Friday to give his side an impressive victory that keeps them two points clear at the top of Group A3.
Marco Rossi's side will qualify for next year's Finals if they avoid defeat at home to Italy on Monday, with the European champions having beaten England 1-0 at San Siro.
It was another memorable evening for Hungary at the Red Bull Arena, while Hansi Flick will be left to rue a night to forget with the World Cup looming.
From the first whistle, Hungary showed a proactive intent, tackling their hosts head-on with great intensity, and their approach was rewarded when Germany were caught napping from a corner 17 minutes in.
Few appeared to expect Szalai's to attack the near the edge of the six-yard box, and the forward's delightful flick to convert Dominik Szoboszlai's delivery sailed beyond Marc-Andre ter Stegen's grasp and into the far corner of the net for a worthy lead.
Germany thought they had equalised through Thomas Muller's strike shortly after the restart, but the goal was ruled out as Jonas Hoffman was offside.
That was as close as Flick's side came to salvaging a point as Hungary held on to keep their fate in their own hands heading into a decisive final group game.
(With OPTA inputs)