Middlesbrough, Youth Cup runners-up to Tottenham Hotspur in 1990, take on Manchester City, winners against Manchester United in 1986, in their first leg match.

Another Manchester derby is a possibility this season, with City and United having avoided each other in the semi-final draw.

Jim Cassell, City's Academy Director, has seen the Middlesbrough youth team in action recently and knows they will be difficult opponents.

"They are a well organised side who are difficult to break down, with a top class international goalkeeper in Ross Turnbull", he said.

"We know we will have to be at our best to beat them and that means the kind of level we found against West Ham (in the quarter-finals)."

Even though the tie is being played over two legs, City will go to the Riverside with the intention of winning the first game.

The return leg will be played at Maine Road on 1st April.

Charlton Athletic entertain Manchester United at The Valley this coming Saturday (3.00pm) in the first leg of the other semi-final.

Like Middlesbrough, Charlton have never won the Youth Cup - but they were runners-up to Coventry City in 1987. United have won it a record eight times. They did with George Best in 1964 and with David Beckham in 1992.

Midfielder Kieran Richardson, who has seen first-team action for United in both the Premiership and the Champions' League this season, could be a key performer this time.

The return will be at Old Trafford on 9th April.

How they got to the semis:-

MIDDLESBROUGH
3rd Round: Bury (h) 3-1
4th Round: Barnsley (a) 1-0
5th Round: Luton (a) 1-1 - won 4-3 on penalties
6th Round: Tottenham (h) 1-0

MANCHESTER CITY
3rd Round: Wrexham (h) 3-0
4th Round: Peterborough (a) 1-0
5th Round: Millwall (a) 1-0
6th Round: West Ham (h) 2-0

CHARLTON ATHLETIC
3rd Round: Cardiff (a) 3-1
4th Round: Wolves (h) 1-0
5th Round: Sunderland (a) 2-2 - won 4-3 on penalties
6th Round: Leeds (a) 1-0

MANCHESTER UNITED
3rd Round: Newcastle (a) 3-1
4th Round: Sheffield Wednesday (h) 2-0
5th Round: Sheffield United (h) 1-1 - won 4-3 on penalties
6th Round: Tranmere (h) 3-1