It was a night to forget in Milan for Gareth Southgate's England side as they were relegated from their Uefa Nations League group following a 1-0 defeat by Italy.
The contest marked just the second meeting between the two teams since that memorable Euro 2020 final under the iconic Wembley arch last year. The Azzuri ran out triumphant that night and they did so again on home soil via a well-taken Giacomo Raspadori strike beyond the despairing dive of Nick Pope.
In truth, England had their fair share of chances but failed to take the game by the scruff of the neck and were eventually punished as a result. Southgate cut a frustrated figure on the touchline as he watched his players fail to execute the game plan yet again.
Giacomo Raspadori's 68th minute strike was enough to resign England to relegation to Tier B of the competition. This has hardly done wonders for the collective feeling of confidence just two months before the Qatar World Cup starts.
Mirror Football has analysed some of the game's winners and losers as fears over England's prospects in Qatar continue to grow.
Gareth Southgate - Loser
Undeniably the biggest loser of them all on the night, Southgate's stock has fallen remarkably since around this time a year ago. The Three Lions boss has overseen one of the worst barren-spells in front of goal of any England side in recent memory.
In fact, it has now been more than seven-and-a-half hours since his side notched a goal from open play. Falling to Italy meant it's three defeats from their last five. It has been five games without a win, which marks England's worst run of form since they were led by Roy Hodgson back in 2014.
That doesn't even tell the full story, if you take into consideration the fact that some of those games under Hodgson were friendlies - Southgate is in the midst of the worst form England have experienced in competitive action since 1992.
Understandably, this is a huge concern with the Qatar World Cup just around the corner. The travelling support made their feelings clear to Southgate come the full-time whistle, though they may be even more upset when they read his post-match comments.
The England boss made a bold claim during his media duties, adding: "I personally thought the performance was a step in the right direction but I perfectly understand that because of the result that's not going to be the reaction."
Harry Maguire - Loser
It does feel as if the much-maligned central defender simply cannot catch a break at the moment, but it was another disappointing display from Maguire.
The Manchester United captain raised eyebrows relatively early on when he needlessly booted the ball out for a corner, putting his side under more pressure, all because he didn't scan his surroundings before volleying the ball behind Pope's goal.
Maguire is yet to win any game for club or country that he has started this season, failing to help United secure all three points from the start in any clash this term - whether that be in the Premier League or in Europe.
While this was by no means the 29-year-old's worst performance, for a player of Maguire's experience you'd like him to be much more of a commanding presence in what was a much-changed back-line against Italy.
Jude Bellingham - Winner
The teenage sensation was a rare bright spark in an otherwise miserable night from an England perspective, with Bellingham showing glimpses of his mercurial midfield talent.
The Borussia Dortmund star is so naturally progressive, as exhibited in Milan as Bellingham constantly tried to drive his England side forward further up the pitch, though it didn't stop them falling to another defeat.
For quite some time many fans and pundits alike have been calling for Southgate to deploy a midfield two consisting of Bellingham and Declan Rice, but Thursday night's findings were hardly promising.
It is clear that there is still some way to go before the young duo can be entrusted to line-up alongside each other in the biggest games, with a certain degree of chemistry lacking despite their overwhelming talent.
Harry Kane - Loser
The Three Lions skipper was starved of service all evening, but on the limited occasions he did get on the ball Kane looked way off the pace.
Whether it was because he spent so long watching the game unfold as a passenger is unclear, but Kane did not have his shooting boots on.
The closest the Spurs star got to adding to his Three Lions tally came when he forced Gianluigi Donnarumma into a smart, if not too testing double-save.
Kane will be more concerned than anyone about England's current form in front of goal, with their last open play effort coming all the way back in March against Ivory Coast - and he didn't even score it, Raheem Sterling did.
His underwhelming night means England's captain remains three goals behind Wayne Rooney as Kane continues his quest to become England's all-time record men's goalscorer.
Raheem Sterling - Loser
Sterling is another prominent figure in an England forward line bereft of goals over the last few months and must take his fair share of the blame.
Thursday night's showing in the San Siro was one of the Chelsea star's worst in a Three Lions shirt for some time, with the technical quality that allowed him to star in a Pep Guardiola side for so long seemingly abandoning him against Italy.
His inability to keep hold of the ball proved a real obstacle to anything England tried to build in an attacking sense and it came as a surprise that Sterling actually lasted the entire 90 minutes.
