Giacomo Raspadori scored the winner in the San Siro as Italy relegated England to League B of the Nations League.
Three games without a win and bottom of their Nations League group is far from ideal preparation as England’s countdown to the finals of the World Cup continued.
Harry Kane rescued a point for England in Germany with a late penalty as Gareth Southgate’s men toiled in Munich.
England lost their opening Nations League game in Hungary with a poor 1-0 penalty defeat at the Puskas Arena.
Phil Foden scored two late goals as England beat 10-man Iceland in a dead rubber UEFA Nations League game at Wembley.