In what is their worst run of form since 2014, England were relegated to the second tier of the UEFA Nations League after another poor display against European Champions Italy.
In a game of few chances, Giacomo Raspadori's curling 68th-minute winner sealed the tie for the Azzurri after he broke past England's back three to slot home in Nick Pope's goal.
England lacked creativity in the middle of the pitch as their best chance of the game came from a late Jude Bellingham header that he sent over the bar.
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The Three Lions have been winless in their past five games and haven't scored a goal from open play in 450 minutes of football.
They have all to play for in their next fixture against Germany, keeping in mind their elevated status as one of the World Cup favourites. A tough test awaits Gareth Southgate's men.