England dropped into the League B of UEFA Nations League after a 1-0 away defeat to Italy while Germany were stunned by Hungary with a 1-0 setback on home soil.
England sat bottom with two points in Group 3 of League A before Friday's game, while Italy ranked third with five points. The two finalists of Euro 2020 played out a goalless tie in the first leg.
Italy entered San Siro without injured Marco Verratti and Sandro Tonali, as Jorginho pulled the string in the midfield and Giacomo Raspadori partnered with West Ham man Gianluca Scamacca up front.
Harry Kane spearheaded England's three-forward line flanked by Raheem Sterling and Phil Foden, reports Xinhua. It was a tedious first half as both sides failed to create too many opportunities, and the most promising chance emerged in the fourth minute when Scamacca saw his header hit the woodwork.
The pace accelerated after the break and the Azzurri went ahead in the 67th minute when Leonardo Bonucci's trademark long pass found Raspadori who took a few touches to release a curler into the net.
In a bid to avoid relegation, the Three Lions strengthened the attack, and goalkeeper Gianluigi Donnarumma needed a double-save to deny Kane while on the other end Manolo Gabbiadini's solo run was smothered by Nick Pope and Federico Dimarco's cross-shot hit the upright.
Elsewhere in the same group, Germany were surprised by Hungary despite over 70 per cent of ball possession. Adam Szalai's smart back-heel flick in the first half killed the game while Thomas Mueller had the ball into the net, but it was wiped out as Jonas Hofmann was offside in the build-up.
"The defeat won't knock us out. It is an eye opener though. We played a terrible first half. The second half was better, but we still couldn't create a lot of dangerous chances," said Germany head coach Hansi Flick.
Italy catapulted themselves into the second place of Group 3 and will take on front-runners Hungary for the top place and the semifinal spot Monday while winless England will host third-placed Germany.