Back in England, Gareth Southgate experienced a sinking feeling that became all too familiar when Reece James hobbled away here at the San Siro. First Kyle Walker, now this.
The Chelsea full-back added to his growing repertoire of impressive performances before running away with what appeared to be a knee injury in the 60th minute.
As Southgate will be hoping for good news when England medics check James’ fitness on Wednesday morning, although the fact the defender was on the pitch after the final whistle and applauding away fans is positive.
Because with or without Walker, an English starting eleven without James seems unimaginable at the moment.
With less than five weeks to go before the Three Lions begin their World Cup campaign against Iran, there’s a chance Southgate might feel the same way. At least one hopes so.
Walker’s importance to England is unquestionable; one of the best right-backs in European football and a mainstay of Southgate’s successful reign.
James has long been considered the heir to Walker’s throne – but we’ve gone beyond that now.
If injury allows, this is James’ time; Whether Walker recovers from a groin injury in time to be included in the Qatar squad should be irrelevant.
That shouldn’t take away from Trent Alexander-Arnold who, despite his current struggles, still has his best days in the England shirt ahead of him.
But for James there has to be a place on the team at the Worlds, no matter what system Southgate uses during the tournament. Southgate will pray he is fit.
Here at the San Siro he patrolled the right flank of the Chelsea team with authority and conviction – not necessarily the easiest thing to pull off in a venue as historic as this.
It was like he owned the place. Not in an arrogant way; His work ethic and willingness to make sacrifices are a key trait in why James is being hailed as one of the best young all-around footballers in the world.
His closest circle, including father Nigel and lawyer Udo Onwere – himself a former footballer – play a key role in James’ down-to-earth approach.
But it’s his natural quality in possession, his ability to choose the right pass that really sets him apart.
In the 19th minute, James scanned his radar and executed. The result: a penalty for Chelsea and AC Milan reduced to 10 men.
Chaos all with a poetic swipe from James’ right boot.
His club manager Graham Potter backed him to become a Chelsea legend after another brilliant performance at home against the Rossoneri last week.
Southgate will be desperate that James’ opportunity to make himself an English legend isn’t cruelly denied him.