Following a 1-0 loss to Italy in the Nations League at the San Siro, the Three Lions of England have been demoted to the UEFA Nations League B.
Prior to the match, the Three Lions needed to at least draw in Milan to have a chance of deciding their fate going into Monday's Group A3 meeting against Germany.
The Italians nearly seized the lead right away in the eighth minute, but Gianluca Scamacca headed Federico Dimarco's cross onto the bar, where Nick Pope provided the slightest of touches to aid it hit the post.
Despite what was at stake, the game struggled to get into life following that early Italy chance as both sides were unable to create many more clear opportunities in the first half.
The Azzurri finally broke the deadlock in the 68th minute, as Giacomo Raspadori fired in a brilliant powerful strike into the far corner from inside the penalty area.
Italy almost doubled their lead with six minutes remaining, but Dimarco’s shot towards the far post came back off the upright.
Roberto Mancini’s side held on to inflict England’s third defeat in five international matches.
Three Lions have now lost three of their last five international matches and have not scored a goal in over 452 minutes of open play in what is their worst run of form in eight years.