Manchester United striker Federico Macheda scored a late penalty as England Under-21s were defeated in their friendly clash with Italy in Empoli.
Shortly after substitute Scott Sinclair had squandered a great chance, Ben Mee brought down Niccolo Giannetti to concede a spot-kick with two minutes remaining. Macheda, who is currently on loan at Sampdoria, made no mistake to deal England a blow in their preparations for this summer's European Under-21 Championship in Denmark.
Manager Stuart Pearce, who saw his squad severely weakened by withdrawals, handed a debut to Middlesbrough defender Joe Bennett while 17-year-old Chelsea midfielder Josh McEachran made his first start. Everton striker James Vaughan, meanwhile, made his first appearance for nearly 18 months after impressing on loan for Crystal Palace.
Italy, who failed to qualify for the European Championships, fielded a team made up largely of teenagers.
A quiet start to the match took a worrying turn for England and particularly Everton after little over 10 minutes when Jack Rodwell appeared to suffer a groin problem and was replaced by Jack Cork.
The only clear-cut chance of the first half fell to Ciro Ferrara's Italy as Gianvito Misuraca found space behind the England defence but Frank Fielding got down well to push his shot around the post.
The visitors managed only brief glimpses of goal, with Vaughan, Marc Albrighton and Henri Lansbury all shooting off target.
The start of the second half saw both Albrighton and Vaughan misplace passes with England in promising positions while Macheda shot into the side-netting.
With an hour gone, Pearce, who celebrated his fourth anniversary as manager on Sunday, made a triple substitution, giving debuts to Jonny Howson, Jay Rodriguez and Alex Oxlade-Chamberlain in place of Vaughan, Lansbury and Nathan Delfouneso.
Highly-rated Southampton youngster Oxlade-Chamberlain made an immediate impact with a run and fizzing cross along the six-yard line but none of his team-mates could get on the end of it.
Sinclair came on for Albrighton with quarter of an hour remaining, and the Swansea winger should have put England ahead with nine minutes left. An excellent through-ball from McEachran found the former Chelsea youngster in acres of space but he shot straight at goalkeeper Carlo Pinsoglio, who then produced another good save from the same player at his near post.
Having stepped up the pace, though, England conceded the only goal of the game in the 88th minute.
Substitute Giannetti ran in behind Manchester City defender Mee, who clearly brought down the striker and was promptly shown a red card, with Macheda easily beating Fielding from the penalty spot.
England Under-21 coach Stuart Pearce believes that in Josh McEachran England have a talent to rival that of Jack Wilshere.
Pearce said: "Chelsea think extremely highly of him and you can see why. He's got the ability and the vision that you know, if players run off of him, he's got the ability to find them with passes.
"All of our cutting passes probably came from him. (Henri) Lansbury has got the benefit of that insight to play those passes but I think, in Josh, he's got a really outstanding talent, similar to Wilshere, and it bodes well for us.''
Pearce hinted McEachran may well have played himself into the Under-21s for the foreseeable future, adding: "He's come in and played outstandingly well, so if I feel as though, if he is going to start for me, then he will be in the Under-21 squad from now on.
"If I feel as though he is going to come in and be a squad player, then there's no need and he will stay with the Under-19s and play football. If he carries on playing like that then it won't be long before he's permanently in the Under-21s side.
"We talk about the lack of talent in England at times, but when you look at the talent of McEachran and Wilshere then I apply one of Sir Trevor (Brooking's) famous old sayings: 'If they were wearing Spanish shirts, you would revere them'.
"They are two outstanding players who can see a pass and see the whole picture better than I can as a coach.''
Pearce's squad was heavily depleted by withdrawals but he praised the players who did turn out and is content with the talent available to him for this summer's European Under-21 Championship.
He said: "Given the amount of players we had pull away from the situation, and injured, I was a little bit disappointed. But once the game got started, and certainly at the end of the game, I was pleased with the contribution of quite a number of them.
"I have learned a lot from this game. We've got some good talent here and this is another part of the player pool that we have got that is fighting for a place at the Under-21 tournament in the summer. The more options and problems I have, the better it is for me and England.''