After 889 minutes without conceding, England were finally breached in spectacular fashion by an Italy side who go straight to the top of UEFA European Under-21 Championship Group A.
Lorenzo Insigne, who missed just one Serie A game for Italian top-flight runners-up SSC Napoli all season, provided the spear that finally punctured England, curling a splendid free-kick beyond Jack Butland. Stuart Pearce's side had no answer and will now go into Saturday's fixture against Norway bottom of their section while Italy face hosts Israel knowing another win would book a semi-final place.
Though England had the first chance of note when Connor Wickham poked straight at Italy goalkeeper Francesco Bardi, Insigne's winner was due reward for the performance of both him and his side. All silky passes and gliding runs, Italy's diminutive No10 dragged a shot wide midway through the first half before going closer still following the cutest of one-twos with Ciro Immobile.
Indeed it was Immobile who had threatened first for Devis Mangia's team, outpacing England left-back Jack Robinson and flashing a shot narrowly past the frame of Butland's goal. The England No1 endured a far busier time than Bardi, whose biggest scare of the first 45 minutes came when Jason Lowe chanced his arm from range.
Spurred on by the energetic Liverpool FC duo of Jonjo Shelvey and Jordan Henderson, England started the second half with more purpose. However, Italy possessed a far sharper cutting edge up front and nearly took the lead once more when Fabio Borini's back-post header was scooped behind by Butland.
Borini was again at the fore when he charged down an England clearance, though he then lacked the composure that his team-mates had showed on the ball all evening. Marco Verratti soon started to find his feet, attempting to unpick the England lock with a nutmeg here and a dinked free-kick there. However, it looked like Italy would go the way of England's previous nine opponents and fail to trouble the scorers. Then, though, with 11 minutes left, Insigne executed his most telling act of a wonderful performance.
Henderson so nearly provided the perfect riposte with a last-gasp set piece of his own, but Bardi was up to the task to ensure Italy face Israel at the weekend in buoyant mood.