Town will face Bristol Rovers or Plymouth Argyle in the third round of the FA Cup if they beat Coventry City at Portman Road in next week's second-round replay.
Like the Blues and the Sky Blues, the League One Pirates and League Two the Pilgrims drew 1-1 in their second-round tie at the weekend and face a replay at Home Park next week.
Town have been paired with Bristol Rovers on four occasions in the FA Cup, most famously in the fifth round in 1978 on their way to their one and only Wembley triumph.
After a controversial in-the-snow 2-2 draw at the Eastville Stadium, the Blues won 3-0 at Portman Road.
A year later, the teams met at the same stage when Town won 6-1 at home.
The Blues were the 2-1 victors in a third round tie at Eastville in 1985, then the teams met again in 1998.
After a 1-1 draw at a freezing Memorial Ground, Town won 1-0 at Portman Road.
More recently the teams met in a League Cup tie in Suffolk in 2012 which the Blues won 3-1.
Town's only previous FA Cup tie against Plymouth was a third-round tie in 1993 which the Blues won 3-1.
Third round ties will take place over the weekend of January 4th. Town’s scheduled league game for that day is already set to be postponed as Fleetwood, who were due to visit Portman Road that afternoon, are through to round three in which they will host Portsmouth.
FA Cup Third Round
Leicester City v Wigan Athletic
QPR v Swansea City
Fulham v Aston Villa
Chelsea v Nottingham Forest
Wolves v Manchester United
Charlton Athletic v West Brom
Rochdale or Boston United v Newcastle United
Cardiff City v Forest Green Rovers or Carlisle United
Oxford United v Exeter City or Hartlepool United
Sheffield United v AFC Fylde
Southampton v Huddersfield Town
Liverpool v Everton
Bristol City v Shrewsbury Town
Bournemouth v Luton Town
Brighton v Sheffield Wednesday
Bristol Rovers or Plymouth Argyle v Coventry City or Ipswich Town
Eastleigh or Crewe Alexandra v Barnsley
Manchester City v Port Vale
Middlesbrough v Tottenham
Reading v Blackpool
Watford v Tranmere Rovers
Preston v Norwich City
Millwall v Newport County
Crystal Palace v Derby County
Solihull Moors or Rotherham United v Hull City
Brentford v Stoke City
Fleetwood Town v Portsmouth
Arsenal v Leeds United
Gillingham v West Ham United
Burton Albion v Northampton Town
Burnley v Peterborough United
Birmingham City v Blackburn Rovers