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.
Moca FC's Baez, Correa sanctioned by Concacaf Disciplinary Committee for violent conduct in Carib Cup semis clash against Cavalier
The Concacaf Disciplinary Committee has sanctioned players Miguel Baez and Jesus Correa of Dominican Republic club Moca FC for incidents that occurred during their Concacaf Caribbean Cup second-leg semi-final match against Jamaica’s Cavalier FC on Thursday, October 30.
After considering the documentation and evidence gathered during its investigation and based on the competition regulations and the applicable disciplinary code, the Disciplinary Committee has imposed Miguel Baez a six-match suspension and Jesus Correa a three-match suspension for violent conduct.
The sanctions include the automatic one-match suspension for the on-field direct red cards given to each player during that 7-0 beating in Kingston.
Both Baez and Correa must serve their suspensions during the upcoming 2024 Concacaf Caribbean Cup third-place matches and future editions of the competition.
Moca FC is scheduled to meet Haiti's Real Hope FC in that home-and-away tie on November 26 and December 3 to determine the next Caribbean representative that will contest next year's Concacaf Champions Cup. Finalists Cavalier and Cibao FC, also of the Dominican Republic, have secured automatic berths.
Meanwhile, the Disciplinary Committee has also warned the players and the club that more severe sanctions could be taken should incidents occur during future matches.
Holders Spain drawn against the Netherlands in Nations League quarters
Reigning champions Spain have been drawn against the Netherlands in the quarter-finals of the Nations League.
Spain won five of their six games in Group A4, and will face the Dutch for the first time in a competitive match since their 5-1 defeat at the World Cup in 2014.
France, who emerged victorious in the 2020-21 edition of the Nations League, will take on Croatia in a repeat of their World Cup final meeting six years ago.
Germany will face Italy while Portugal, who were the inaugural winners of the tournament, were drawn against Denmark, with the two-legged fixtures taking place in March.
The semi-finals are single legs which will get underway in June, with the third-place play-off and final to be played three days later.
European champions Spain, Portugal and Germany topped their groups without losing a game to go into the seeded teams' pot along with France.
The winner of Spain's enticing tie with the Netherlands will play either France or Croatia, while Cristiano Ronaldo will be looking to inspire Portugal to a second title.
Only Sweden's Viktor Gyokeres (nine), Norway's Erling Haaland (seven) and Romania's Razvan Marin (six) have scored more goals in this year's edition than Ronaldo (five).
Scotland, who finished third in Group A1 behind Portugal and Croatia, will face Greece in a Nations League play-off to remain in the top tier of the competition.
The other play-off games will see Turkey face Hungary, Ukraine take on Belgium, and Austria square off against Serbia in March.
Schwarz believes pressure will bring out the best in Red Bulls
New York Red Bulls head coach Sandro Schwarz says pressure is good for players as they prepare to face rivals New York City FC in the MLS Eastern Conference semifinal.
The Red Bulls beat defending MLS Cup champions Columbus Crew 1-0 in the first of their best-of-three series before edging them 5-4 on penalties in Game 2.
They are playing in the semifinals for the first time since 2018, though it is the first time they are meeting their city rivals in the postseason in their history.
Schwarz acknowledged there was a lot riding on this game but is sure the pressure can bring out the best in his team.
"To feel the pressure as a player and head coach is good," he told reporters. "We need the pressure to bring our best performance and level.
"Without pressure, it's not possible. Now we have this historic derby on Saturday and we're very excited.
"Our main target is to win this game, but our focus is to get a result like we had against Columbus. The last three weeks have been looking at how we can create our best performance for Saturday."
Meanwhile, NYCFC had to come from behind in round one after losing their first match to FC Cincinnati but won the second at home before going through with a 6-5 penalty shootout win in the decider.
Head coach Nick Cushing is delighted to have home advantage for the semifinal tie but says he is not yet thinking about securing the same fate in the next round.
"I've learned over my tenure here as assistant coach and as head coach that the next game is the most important part," Cushing said.
"The whole focus is hosting a playoff semifinal at home. We're really proud that we've done everything to get to this opportunity, but there are many more challenges ahead, and we cannot look further than the first 10 minutes of the game, because that is our main focus.
"And then, through there, we have a game plan and half-time. We're working through this game, and that is our whole focus."
PLAYERS TO WATCH
New York City FC – Alonzo Martinez
Twelve of Alonzo Martinez's 17 goals this season (regular season and playoffs) have been scored in home matches, while Santiago Rodriguez has scored 11 of his 13 goals at home.
Both players found the net in NYCFC's home win over Cincinnati in Game 2 of their first-round series.
New York Red Bulls – Emil Forsberg
Emil Forsberg became the 14th different Red Bulls player to record a goal and an assist in a single playoff match in Game 2 of New York's first-round series against Columbus Crew.
No player has more than one such game in the team's postseason history.
MATCH PREDICTION: NEW YORK CITY FC WIN
This will be the first playoff meeting between New York City FC and the Red Bulls, but the fifth in knockout rounds in all competitions.
The Red Bulls eliminated NYCFC in each of the previous four knockout round meetings, doing so in the US Open Cup three times and the Leagues Cup once.
NYCFC has won five of their eight all-time home playoff matches, including the last three in a row. All three teams that defeated NYCFC on the road in the playoffs went on to reach the MLS Cup Final (Toronto FC in 2016 & 2019, Atlanta United in 2018).
The Red Bulls' 1-0 win at Columbus in Game 1 on October 29 ended a six-match road losing streak in postseason play for the club. The Red Bulls have won multiple road playoff games in a single season twice before, doing so in 2008 and 2017.
OPTA WIN PROBABILITY
New York City FC – 46.5%
Draw – 26.5%
New York Red Bulls – 27%
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