The young royal was smartly dressed in a suit and tie as he joined his parents to cheer on the mighty Lions. And initially it all seemed to be going like a dream, as Luke Shaw popped up to half-volley home Kieran Trippier's cross in the second minute. George, seven, enthusiastically celebrated the goal, beaming and hugging his mum, as Wembley exploded in euphoria.
But the Italians fought back in the second half, equalising through Leonardo Bonucci, the veteran Juventus defender.
After the teams remained deadlocked at the end of extra-time, a penalty shootout ensued.
In a dramatic finale, the Azzurri won through 3-2, breaking English hearts yet again.
Prince George appeared devastated along with his mother, the Duchess of Cambridge, who was pictured with her hands in her face.
Prince William placed his hands reassuringly on the shoulders of his eldest son, as he tried to ease his pain.
A forlorn George was pictured with eyes cast down as the disappointment sank in.
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After the match, the Duke of Cambridge issued a rallying call to England's brave warriors.
Describing the loss as "devastating", the Duke wrote in a tweet: "@England, you’ve all come so far, but sadly this time it wasn’t our day.
"You can all hold your heads high, and be so proud of yourselves — I know there’s more to come. W"
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William, who is President of the FA, also graciously congratulated the Italians on their achievement.
"Congratulations @Azzurri on a great victory," he added.
Fans were quick to echo the Duke of Cambridge's sentiments, as they flooded the social media airwaves with messages of support.
One posted: "Proud of the team. You made history to get this far."