Town have drawn League Two Portsmouth at Portman Road in the third round of the FA Cup.
The teams have met in the FA Cup on two previous occasions, both within the last 10 years on Suffolk soil when the visitors were in the Premier League.
The Blues played Pompey at the third round stage in 2007/08 when the visitors won 1-0 via a David Nugent goal, Liam Trotter having been controversially sent off in the first half.
Pompey also visited Portman Road at the same point in the competition two years prior to that when a Dario Silva goal saw the Hampshire club to another 1-0 victory.
The teams most recently met in the Championship in the 2011/12 campaign when Town won both games 1-0, Keith Andrews netting the goal at home and Michael Chopra at Fratton Park.
Historically, the Blues have won 19 games between the two clubs (18 in the league, one in the League Cup), 11 have been draws (11) and Pompey have won 11 (nine in the league plus the two FA Cup ties).
Blues defender Matt Clarke is currently on loan with Portsmouth but his half-season spell is set to end on January 3rd, prior to the FA Cup third round and even if his time there is extended he wouldn't be able to face his parent club.
The Pompey squad also includes ex-Blues Brian Murphy and Gary Roberts, while former academy striker Caolan Lavery is on loan from Sheffield Wednesday.
Portsmouth beat Macclesfield 2-1 at home in round one and Accrington Stanley 1-0 in the second round, also at Fratton Park.
Third round ties will be played between Friday 8th and Sunday 11th January.
Meanwhile, James Alabi’s loan club Grimsby Town are in second round action on TV this evening when they take on Shrewsbury at Blundell Park (BT Sport 2, KO 7.45pm).
FA Cup Third Round Draw
Watford v Newcastle
WBA v Bristol City
West Ham v Wolves
Salford or Hartlepool v Derby
Exeter v Liverpool
Tottenham v Leicester
Colchester v Charlton
Peterborough v Preston
Northampton v MK Dons
Arsenal v Sunderland
Newport v Blackburn
Ipswich v Portsmouth
Birmingham v Bournemouth
Wycombe v Aston Villa
Sheffield Wednesday v Fulham
Oxford v Swansea
Brentford v Chesterfield or Walsall
Bury v Bradford
Manchester United v Sheffield United
Everton v Dagenham or Whitehawk
Southampton v Crystal Palace
Eastleigh v Bolton
Nottingham Forest v QPR
Carlisle v Yeovil
Chelsea v Leyton Orient or Scunthorpe
Doncaster v Stoke
Leeds v Rotherham
Cardiff v Grimsby or Shrewsbury
Huddersfield v Reading
Middlesbrough v Burnley
Norwich v Manchester City
Hull City v Brighton