This was supposed to be Jude Bellingham’s big chance. An opportunity to show he’s ready for the World Cup.
Unfortunately, it was also the night when Gareth Southgate asked the teenager and his central midfield partner Declan Rice to do a three-man job. Bellingham did what he could to press his claim for a starting place in England’s team for Qatar.
His workrate and attitude never faltered. If it wore Azzurri blue, it got tackled. But the Brummie who once told a Borussia Dortmund team-mate that he was f*****g s**t” will know this isn’t the form England will want to take into the biggest tournament of all.
Giacomo Raspadori’s second-half strike gave Italy a victory that leaves England with just a single point from five Nations League games and ultimately relegated. Bellingham had a chance to equalise in injury-time, but sent his header onto the roof of the net.
A player of his talents should have done better. But that was England's story in a nutshell in the San Siro. For the millions of fans hoping to still be wearing Three Lions on their chest on December 18, this was a worrying performance - both individually and collectively.
Southgate clearly feels that a three-man defence offers him his best chance of success in the desert. But even against an uninspired Italy side currently being rebuilt by Roberto Mancini, it seemed England were playing on quicksand.
The manager now only has Monday night’s game against Germany to make some adjustments. Southgate will be worried how his system left Bellingham and Rice exposed too often.
Italy always had a man spare - and usually it was the passing metronome that is Jorginho. This isn’t the Italy that won the Euros at Wembley. And they won’t even be going to the World Cup. But they still prevailed.
England’s two midfielders were reduced to harrying and carrying, forced to do the dirty work and leave Harry Kane, Raheem Sterling and Phil Foden to live off scraps.
Bellingham is a box-to-box throw-back to the days when midfield players were expected to do it all. And even at the tender age of 19, the growing maturity of his performances for Borussia Dortmund suggest he has it in his locker.
To his credit, he quickly realised the need to sit in to protect Kyle Walker, Eric Dier and Harry Maguire as they struggled to get to grips with their own doubts and demons.
Particularly in the opening stages, when Italy couldn’t believe the chaos even the most simple forward ball was creating for the visitors.
Like England, Bellingham gradually grew into the game. One clever link-up with Foden saw him thread a perfect pass into the path of Reece James only for the wing-back to fail to find Harry Kane with his cross.
Another smart combination with Foden ended with him feeding Kane down the right only for the England skipper to be wasteful. It was more of the same in the second half. Two teams who knew what they wanted to do but couldn’t execute the plan.
It had all the hallmarks of a relegation battle. Which, given both countries' position in the Nations League table, it was. Bellingham got a painful boot in the head on the hour when he ducked bravely into a challenge.
After a worrying few minutes which saw even Italy’s players calling for the medics, he was up and running again. But England were down and out in the 67th minute after being undone by Leonardo Bonucci’s routine long ball over the top and Raspadori’s ability to shake off Walker and leave Nick Pope beaten.
Almost immediately Southgate went to a back four. And Bellingham was able to free Kane to force Gianluigi Donnarumma into two saves when the England skipper really should have been trying to find a team-mate with a cross.
Even before it emerged that Kalvin Phillips needed surgery to repair a damaged shoulder, Bellingham was building a compelling case to start against Iran on November 24 with the quality of his performances in Germany. He will certainly have better nights wearing an England shirt. Hopefully in the Middle East.