England suffered the ignominy of relegation in the Nations League following a 1-0 defeat to Italy but more concerning for Gareth Southgate than a potentially tougher route to the next European Championship is his side’s dismal form going in to the World Cup and the wavering support of even England’s travelling supporters.
Giacomo Raspadori’s brilliant 68th-minute strike at San Siro condemned England to a fifth game without a win -- their worst run under Southgate and since 2014 -- and they have just one more fixture to arrest the slump before Iran await in their opening match in Qatar on November 21.
Southgate faced boos and jeers from the casual home support after England’s last outting -- the wretched 4-0 defeat to Hungary at Molineux -- and he was booed by the away fans in Milan as he went to applaud them at the final whistle.
In a ragged first-half, short of chances at either end, it was difficult to believe that these teams contested a European Championship final just 14 months ago but Italy grew into the game while England faded, and the hosts should have won more comfortably after a flurry of late chances.
It is a shame that Roberto Mancini’s side will not be in Qatar, although they have the excuse of a hangover from winning the Euros and being a side in transition.
It is less easy for Southgate to explain away England’s shortcomings, and there is now real pressure on the manager to get a result in the final game of this Nations League group against Germany at Wembley on Monday.
Towards the end of the opening 45 minutes, England surpassed 400 minutes without a goal from open play, suggesting their failings during a dismal June camp are more deep-rooted than Southgate had suggested at his pre-match press conference.
The England manager used the occasion to claim that he knew the reasons for the team’s struggles in the summer, when they went four games without a win or goal from open play, culminating in the defeat at Molineux.
He also suggested he had "compromised" on his beliefs during the run, and England’s initial approach marked a return to something more classically Southgate: a solid defensive unit anchored by a back three, with quick forward players searching for counter-attacks and opportunities from set-pieces.
The manager’s critics believe this approach is simply not sufficient given the talent at his disposal; that he is too safe, too cautious.
And there was little here in the way of a counter-argument. Clearly England are playing far worse than the sum of their glittering parts at present, with Southgate failing to maximise the talent of the likes of Harry Kane, Bukayo Saka and Raheem Sterling, who were all quiet.
The positives were limited to the rare occasions when Phil Foden or Jude Bellingham managed to get on the ball, and particularly when they combined, leaving the visitors briefly looking capable of creating meaningful chances, but these moments were few and far between.
Generally, it was stodgy, with Kane given short change by Italy’s back-three and largely reduced to hopeful pot-shots. When the England captain did get a sight of goal with Italy already leading, Gianluigi Donnarumma made a solid double save from his angled strikes.
An exciting-looking wing-back pair of Reece James and Saka -- named England’s player of the year pre-match -- were barely troubled Italy in the final third at all, while Declan Rice and Bellingham left too much space in the midfield for Italy’s pass-masters to operate.
Even England’s defence, which was solid until Raspadori brilliantly made space in the box and curled into the side-netting, crumbled in the final 20 minutes.
Under-pressure Harry Maguire -- who was twice beaten by Italy forwards in the opening five minutes only for Nick Pope to twice save -- appeared predictably short of confidence, while Eric Dier initially looked assured in his first cap in two years but was dragged out of position ore than once as Italy pushed forward late on.
In the end, the biggest positive for England was that the scoreline was not more damning, as the Azzurri threatened to add to their lead, Frederico Dimarco going closest to a second when his cross-shot came back off the post.
England could now face the likes of Georgia and Kazakhstan in the next iteration of the Nations League, and a top opponent in qualifying for Euro 2024.
Really, that is unlikely to matter much and perhaps nor does England’s current form, provided they deliver in Qatar as they have done in the last two major tournaments under Southgate.
Nonetheless, result in Milan leaves Southgate with mounting questions all over the pitch and running out of time to find answers.