Town's U18s will face Southampton or Watford at home in the fifth round of the FA Youth Cup if they defeat Crystal Palace at the fourth round stage at Portman Road on Tuesday, 20th January (KO 7pm).
Ronan Murray scored the only goal from the penalty spot as the U18s defeated Shrewsbury 1-0 at Portman Road in the third round.
The Blues' youngsters beat Watford 3-1 at home in the fourth round of last year's competition, while their last FA Youth Cup meeting with Southampton came in the 2005 final, the Blues winning 3-2 over two legs. The Saints take on the Hornets at St Mary's on Tuesday in their fourth round tie.
No date has yet been set for the fifth round match but games must be played before Saturday, 31st January
FA Youth Cup Fifth Round
Ipswich Town/Crystal Palace v Southampton/Watford
Bristol Rovers/Liverpool v Chelsea/Walsall
Preston North End/Sunderland v Arsenal/Wolverhampton Wanderers
Plymouth Argyle/Millwall v Charlton Athletic/Tottenham Hotspur
Burnley/Everton v Norwich City
Portsmouth/Manchester City v Queens Park Rangers/Newcastle United
Middlesbrough/Nottingham Forest v Bolton Wanderers/Hull City
Cardiff City/Tranmere Rovers v Birmingham City/Crewe Alexandra