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England suffered the ignominy of relegation from the Nations League’s top tier after a tepid defeat to Italy that raises further concern ahead of the winter World Cup.

Among the favourites to triumph in Qatar having reached the semi-finals four years ago and the Euro 2020 final, things have gone awry for Gareth Southgate’s side of late.

England failed to win any of their four June fixtures and produced a meek response to their 4-0 Molineux mauling against Hungary, with Giacomo Raspadori sealing Roberto Mancini’s Italy a 1-0 victory on Friday night.

A fifth straight match without a win means Southgate’s men have been relegated from Group A of the Nations League – a competition they finished third in three years ago – with a game to spare.

Demotion is embarrassing but the performance is arguably of more concern given it is just 59 days until their World Cup opener against Iran.

The Euro 2020 finalists had played out a forgettable goalless draw behind closed doors in June and the first half in Milan somehow managed to be even more dreary as England toiled against the absentee-hit Azzurri.

It did not get any better from the visitors’ perspective as Italy, who will not be in Qatar, kept them at bay and secured victory through Raspadori’s fine effort.

Harry Maguire
Harry Maguire started in Milan (Antonio Calanni/AP).

Southgate’s side lacked the ruthlessness called for on the eve of a San Siro encounter that ends with more questions than answers, with just Monday’s home match against Germany to come before the World Cup.

Bukayo Saka, named England men’s player of the year earlier in the day, was deployed at left wing-back at San Siro, where Eric Dier won his first cap since November 2020 among six alterations from the Hungary humbling.

Harry Maguire was another brought in and the out-of-favour Manchester United captain’s name was sung by the 4,415 travelling fans in an expression of support that followed Southgate’s public backing on Thursday.

The 29-year-old settled after a shaky start as Italy began on the front foot, with Gianluca Scamacca all too easily beating him to a deep Federico Dimarco cross from the right.

Harry Kane sent a long-range effort over the bar as England toiled
Harry Kane sent a long-range effort over the bar as England toiled (Nick Potts/PA).

A combination of Nick Pope, deputising for the injured Jordan Pickford, and the woodwork denied the West Ham striker’s powerful header at his near post before the frontman struck wide from distance.

England quelled that storm and began to enjoy periods of possession, albeit without injecting creativity and excitement into their play.

Cumbersome with the ball, there was precious little to note in terms of chances beyond Jude Bellingham’s strike into the ground and Harry Kane lashing over from distance.

Thankfully there was no additional time at the end of a wretched first half.

Leonardo Bonucci (left) and Raheem Sterling battle for the ball
Leonardo Bonucci (left) and Raheem Sterling battle for the ball (Nick Potts/PA).

Dier produced an important block and Reece James woefully overhit a well-placed free-kick after Leonardo Bonucci had tripped Raheem Sterling on the edge of the box.

Phil Foden threw his hands in the air in frustration as Kane took a shot from an acute angle when he was free at the back post as the visitors’ disjointed display continued.

England were fortunate that a mixture of the offside flag and Nicolo Barella’s poor finishing prevented them falling behind in the 57th minute after Dimarco was put free to send a pinpoint cross to the far post.

Play had now become ragged and stretched, swinging from end to end without much quality. Rafael Toloi prevented Saka reaching a Kane cross before substitute Wilfried Gnonto’s fierce drive forced a fine block.

Italy’s Giacomo Raspadori celebrates his winning goal
Italy’s Giacomo Raspadori celebrates his winning goal (Nick Potts/PA).

The deadlock was finally broken in the 68th minute as the Azzurri struck.

Bonucci’s long ball put Raspadori in behind Kyle Walker, with the forward keeping his cool before sending a lovely strike beyond Pope from just inside the box.

Kane forced Gianluigi Donnarumma into a double save as England hunted a leveller, with former Southampton forward Manolo Gabbiadini seeing a shot saved by Pope at the other end before Dimarco’s cross-shot hit a post.

Declan Rice saw a hopeful stoppage-time effort saved and Bellingham headed over as Italy saw out victory, leaving the travelling hordes audibly frustrated at full-time.