England suffered the embarrassment of relegation from their Uefa Nations League group after slumping to defeat against Italy in Milan.
Giacomo Raspadori’s stunning 68th-minute strike broke the deadlock in the San Siro as a game that lacked any spark finally came to life after the break, with England’s winless streak extended to five games, their worst since June 2014.
Raspadori produced instant control and a fierce right-foot finish which gave goalkeeper Nick Pope, in for the injured Jordan Pickford, no chance.
Manager Gareth Southgate kept faith with Harry Maguire despite his struggles at Manchester United, the defender suffering one anxious early moment when West Ham United striker Gianluca Scammaca beat him in the air at the far post, only for a combination of Pope and the woodwork to keep his header out.
England responded at last, Italy keeper Gianluigi Donnarumma producing a fine double block from Harry Kane, although the home side had chances of their own in a frenetic finale.