Town have drawn League One Accrington Stanley away in the third round of the FA Cup.
The Blues have never played Kayden Jackson and Janoi Donacien's former club Stanley in a competitive fixture. The duo helped John Coleman's side to the League Two title last season.
Donacien is still on loan from the Lancastrians with his permanent leave to remain - which will trigger the formalising of his £750,000 permanent switch - yet to be confirmed. In the FA Cup parent clubs decide whether their loanees can play against them, which in the circumstances Stanley would appear likely to do.
No current Accrington player has been with the Blues, although keeper-coach Tony Warner had a trial with Town in 1998.
Third round ties are set to be played between Friday 4th and Monday 7th January.
Town's last victory in the tournament came back in January 2010 when they beat Blackpool 2-1 in the third round at Bloomfield Road during Roy Keane’s time in charge.
Last season the Blues were beaten 1-0 at home by Sheffield United, their 13th match without a victory in the competition they won for the only time in 1978.
FA Cup Third Round Draw
Accrington v Ipswich.
Aston Villa v Swansea.
Bolton v Walsall/Sunderland.
Bournemouth v Brighton.
Brentford v Oxford.
Bristol City v Huddersfield.
Burnley v Barnsley.
Chelsea v Nottm Forest.
Crystal Palace v Grimsby.
Derby v Southampton.
Everton v Lincoln.
Fulham v Oldham.
Gillingham v Cardiff.
Guiseley/Fleetwood v AFC Wimbledon.
Man City v Rotherham.
Man Utd v Reading.
Middlesbrough v Peterborough/Bradford.
Millwall v Hull.
Newcastle v Blackburn.
Norwich v Portsmouth.
Preston v Doncaster.
QPR v Leeds.
Sheff Utd v Barnet.
Sheff Wed v Luton.
Shrewsbury v Stoke.
Solihull/Blackpool v Arsenal.
Tranmere/Southport v Tottenham.
West Brom v Wigan.
West Ham v Birmingham.
Woking v Watford.
Wolves v Liverpool.
Wrexham/Newport v Leicester