The Three Lions that faced Italy in a Euros final just a little over a year ago found themselves being booed off the pitch following a dismal display at the San Siro.
Plenty of players that started the match had much to prove. Harry Maguire and Luke Shaw have seldom started for Erik Ten Hag at club level, while Eric Dier returned to the side after 20 months out.
Yet, England looked an uninspired side and lacked a cutting edge for much of the game, making it seven hours of football without a goal from open play by the full time whistle in Milan.
Meanwhile, Italy bounced back from their loss against Germany in June well and even after going ahead had the clearer chances of the two sides.
Roberto Mancini's side, who are not going to the World Cup, moved up to second in League A Group 3 and will have the chance to top the group when they play surprise leaders, Hungary.
Story of the Match
Gianluca Scamacca went close for the home side in the opening stages, his header at the back post from inside the six-yard box was well saved by Nick Pope
However, for the opening 20 minutes of the game both sides were sloppy in possession with a close range header from Harry Maguire the best opportunity for Gareth Southgate's Three Lions.
The remaining 25 minutes of the first half still left much to be desired in the way of attacking football, with both sides continuing to give the ball away cheaply.
Harry Kane had a shot in anger on the 40 minute mark as he led a counter attack from around 30-yards out which sailed over the bar and wide. A move that just about summed up England's first half performance.
The game opened up more in the second half, albeit in a minor way. A jinking run from Raheem Sterling resulted in a freekick on the edge of the Italy box which Reece James sent over the bar.
Italy were showing that they still had teeth, with Nicollo Barella missing from six-yards out on the stretch, however his blushes were saved by the linesman for an offside in the build up.
The most stale of stalemates was broken in the 67th minute when Giacomo Raspadori brought down a long pass before shifting a yard on Kyle Walker to rattle a shot past Nick Pope in the England goal.
England began to get a hold of the game as Italy began sitting back with a double save from Gianluigi Donnarumma denying Harry Kane from a tight angle.
The Italians still showed they were a threat on the counter attack however, with substitute Manolo Gabbiadini missing a 1v1 as England waited for an offside flag that never arrived.
Federico Dimarco hit the post with a low driven effort with just five minutes of normal time left to play. Gareth Southgate's side were lucky to still be in the game.
Jude Bellingham headed over the bar in the final moments of the game but it was Italy that held out to take the victory.
As the full time whistle blew, a huge roar of appreciation went up from the Italian fans, while England's travelling support booed the team off the field. They have just one more game until they will be playing World Cup football.
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Player of the Match - Giacomo Raspadori
In a game that lacked individual quality, Raspadori took the game by the scruff of it's neck and made it his with a fabulous goal from 18-yards out.
Throughout the game, the 22-year old had lots of nice touches and helped massively to bring his teammates into play, allowing his side to sustain attacks.
A special mention must go to Federico Dimarco who was a constant thorn in the side of England down the left-hand side but Raspadori's inspired moment of quality was the difference between the two sides on the night.
Meanwhile, the string of losses and poor performances will have England fans worried as they go in to their last match before the World Cup in December against Germany on Monday.