England suffered the indignity of relegation as a 1-0 defeat against Italy sent Gareth Southgate's side tumbling into the second tier of the Nations League on Friday night.
Neither side threatened to break the deadlock in a dire first-half, but Giacomo Raspadori found the net in style in the 68th minute to condemn the Three Lions to another defeat - a result that means England will start the next Nations League campaign in Tier B.
With the World Cup looming large on the horizon, Mirror Football takes a look at five talking points from disappointing night for England, who are winless in five and entertain old rivals Germany at Wembley on Monday...
More questions than answers
Even before Friday night's match had kicked off, it became clear that England fans would be left with more questions than answers ahead of the World Cup.
Ivan Toney was surprisingly omitted from England's 23-man squad for Friday's meeting after earning his maiden international call-up. While Harry Kane's spot as England's main man is assured, this week's double-header was the perfect stage to gauge whether or not Toney is capable of deputising for the Three Lions' No.9. Instead, he will have just one game to make an impression.
In terms of starting spots, the left-wing back berth seems to be up for grabs in the wake of Luke Shaw's poor start to the season with Manchester United. Yet it was Bukayo Saka, Arsenal's right winger, who was deployed in the position ahead of Shaw and Ben Chilwell, who had seemed the most likely to deputise for Shaw in Italy.
Join the debate! What did you make of England's performance against Italy? Let us know here.
Is Southgate planning to utilise Saka as a wing-back in Qatar? Because if not, with just one more match remaining before the World Cup, surely it would have been far more beneficial to give Chilwell a run out following his extended spell on the sidelines.
Saka, who was crowned England's Player of the Year prior to the match, surely deserves better than to be pigeon-holed into a position that doesn't suit him. England need his guile and quality in the final third, not deep inside his own half.
There are still question marks remaining over key positions in the England squad - and Southgate is running out of time, and opportunities, to work out solutions.
Maguire backing backfires
Southgate was always likely to stick with Harry Maguire in spite of his woes at Manchester United; an approach he has previously taken with Jordan Pickford, who has never let his country down despite his chequered form at Everton prior to this year.
But unlike Pickford, Maguire did little to silence his critics on international duty - and it's becoming abundantly clear that the beleaguered centre-half should be nowhere near this England team when the World Cup kicks off in Qatar in two months time.
He received vociferous backing from the travelling England faithful before the match, but he failed to inspire confidence on the left-hand side of England's back three.
He lost track of Gianluca Scamacca and then Giovanni Di Lorenzo inside the opening five minutes at the San Siro and although he settled down as the match went on, was outshone by the impressive Eric Dier - who may have leapfrogged his England teammate off the back of a sterling display in the San Siro.
Pope stakes his claim
Nick Pope and Aaron Ramsdale have both won plaudits in the opening weeks of the new Premier League campaign, but it was Pope who got the nod to deputise for Pickford in between the sticks.
And the Newcastle shot-stopper did his chances of claiming the No.2 spot no harm with an accomplished display.
Pope did everything that was asked of him and more to nudge ahead in the international rankings - although Ramsdale could be yet be given a chance to stake a claim of his own against Germany on Monday.
Youngsters lead the charge
On a pretty rotten night for England, the performances of Phil Foden and Jude Bellingham should provide leave fans enthused for the future.
Foden is a pivotal cog in the Manchester City team that has dominated the Premier League but has struggled to nail down a regular spot in the national team, while Bellingham has become almost impossible to ignore following his impressive exploits in Germany with Borussia Dortmund.
Both staked their claim for a regular role in Milan - and this evidence it's hard to see why either should not be firmly in Southgate's mind for the opening match against Iran in November.
Foden was busy and by far England's most dangerous player on the night while Bellingham showed why he is the man most suitable to partner Declan Rice with Kalvin Phillips' place in doubt.
Southgate under pressure
Just 14 months ago, Southgate was just one game away from immortality and the toast of the nation - but the England manager is now under significant pressure following another sobering result in the Nations League.
Southgate was booed back in June off the back of a chastening 4-0 defeat against Hungary in the Nations League and this abject showing against the European champions will have done little to dampen the discontent surrounding him.
England have now gone over 450 minutes without a goal in open play and now have a relegation on their hands - hardly ideal preparation for a World Cup.
