England are now without a win in their last five matches after defeat to Italy saw Nations League relegation confirmed.
The poor run of form – their longest without a competitive win since 1992 – could not have come at a worse time, with the World Cup on the horizon.
Manager Gareth Southgate insists the 1-0 defeat at San Siro was a step in the right direction but it has not stopped him and his team coming under pressure.
Here, the PA news agency takes a look at what has gone wrong since England reached the final of Euro 2020 last summer.
Harry Kane’s penalty equaliser away to Germany in June is the only goal England have scored in their five Nations League group matches, with only the reverse fixture remaining.
Having rounded off their World Cup qualifying campaign with a 10-0 win over minnows San Marino, competitive goals have dried up.
Kane, just three shy of Wayne Rooney’s all-time record of 53 England goals, has rarely had a sniff of late, with the likes of Raheem Sterling, Bukayo Saka, Phil Foden and Jack Grealish also drawing blanks.
When Southgate first took the reins in 2016, he said he would prioritise form over favouritism when it came to selecting his squads.
That approach has certainly been questioned of late, with Manchester United captain Harry Maguire starting in Italy despite being out of form and ultimately dropped by his club in recent weeks.
Other names caused a stir when he picked his 28-man squad for this Nations League double-header and, while Brentford striker Ivan Toney was rewarded for his fine form with a maiden call-up, he was left out of the squad altogether against Italy, just when England are striving for the scoring touch.
Southgate has had fitness issues to contend with.
Kalvin Phillips starred in the European Championships, but the Manchester City midfielder could now miss out on a place in Qatar having undergone surgery on a shoulder injury.
Jordan Henderson was included in the squad despite a hamstring problem which has ruled him out for Liverpool of late, while left-backs Luke Shaw and Ben Chilwell have also been sidelined and first-choice goalkeeper Jordan Pickford is out with a thigh complaint.
With just 90 minutes of football between now and their opening World Cup group game match against Iran, Southgate is still tinkering in a bid to find his best formula for success.
This is no more evident than in defence, where it appears he is still undecided on whether a back four or a three-man back line is the way to go.
He switched between the two systems in Milan, with both offering differing lists of positives and negatives as Southgate strives to get his major players into his starting XI, an issue which is clearly causing problems at both ends of the pitch.
Supporters voicing concerns
Southgate has certainly bridged the gap between the England team and their supporters since taking the job.
The run to the 2018 World Cup semi-finals saw some recreate Southgate’s dress, donning waistcoats and penning their own chants for the man who took England so close in Russia.
There were seeds of discontent during the Euros, even if England did ultimately make the final only to lose on penalties.
But the 4-0 loss to Hungary in June saw a minority turn on Southgate, jeering and singing “you don’t know what you’re doing”, the boos returning in Italy as the beleaguered manager applauded the away fans, with those previous rifts threatening to resurface with the World Cup just around the corner.