Pompey have been drawn away to fellow League One side Fleetwood in the third round of the Emirates FA Cup.
The tie will take place at Highbury Stadium on the weekend of January 3-6.
It will be the first ever clash between the sides in the cup, with the previous six encounters all taking place in the league.
The sides have not yet met this season, with Fleetwood calling off last month's scheduled Fratton contest because of international call-ups.
But Pompey won both fixtures last term, including a 5-2 triumph on Town's patch just after Christmas.
Joey Barton's side currently sit seventh in the League One standings, having collected two more points than the Blues.
They have reached this stage of the competition with away victories over Barnet (2-0) and Crawley (2-1).
Pompey – who lifted the FA Cup in 1939 and 2008 – have seen off non-league sides Harrogate Town and Altrincham.
The draw took place at Manchester City's Etihad Stadium and was conducted by Micah Richards and former Blues boss Tony Adams.
A confirmed date and ticket information will be announced in due course.
Please note that a new date will now have to be found for the League One match against Doncaster previously scheduled to take place on January 4.
| Emirates FA Cup third round draw |
| Leicester City v Wigan Athletic |
| Queens Park Rangers v Swansea City |
| Fulham v Aston Villa |
| Chelsea v Nottingham Forest |
| Wolverhampton Wanderers v Manchester United |
| Charlton Athletic v West Bromwich Albion |
| 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 |
| AFC Bournemouth v Luton Town |
| Brighton & Hove Albion 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 Hotspur |
| Reading v Blackpool |
| Watford v Tranmere Rovers |
| Preston North End 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 POMPEY |
| Arsenal v Leeds United |
| Gillingham v West Ham United |
| Burton Albion v Northampton Town |
| Burnley v Peterborough United |
| Birmingham City v Blackburn Rovers |