Pompey have been drawn away to Norwich in the third round of the Emirates FA Cup.
The tie will take place at Carrow Road on the weekend of January 5, with ticket information to be announced in due course.
It ensures a contest between the current leaders of both the Championship and League One.
Pompey's assistant manager Joe Gallen said: "There are big jumps between all the leagues, so we know it's going to be a tough game.
"The Championship is a notoriously competitive division and one we aspire to reach, so the fact they're top of it shows what a big club they are.
"But we've also had an encouraging season to date and I'm sure we'll go there full of confidence."
"The Championship is a notoriously competitive division and one we aspire to reach, so the fact they're top of it shows what a big club they are."
The sides have not met since both were in the second tier during the 2010/11 campaign, with each winning on the other's patch.
Dave Kitson and Greg Halford were on target for the Blues in a 2-0 victory in Norfolk, although the Canaries would go on to secure automatic promotion to the top-flight with a triumph at Fratton Park.
It is Norwich who just shade things in overall contests, with 23 wins compared to 20 for Pompey, while there have been 15 draws.
But you have to go all the way back to the 1949/50 season to find the only games that took place in the FA Cup.
The Blues needed a replay before progressing to the fourth round and although they eventually fell to Manchester United, could console themselves with a second successive Football League title.
|Emirates FA Cup third round draw|
|Bolton Wanderers v Walsall or Sunderland|
|Millwall v Hull City|
|Gillingham v Cardiff City|
|Brentford v Oxford United|
|Sheffield Wednesday v Luton Town|
|Manchester United v Reading|
|Everton v Lincoln City|
|Tranmere Rovers or Southport v Tottenham Hotspur|
|Preston North End v Doncaster Rovers|
|Newcastle United v Blackburn Rovers|
|Chelsea v Nottingham Forest|
|Crystal Palace v Grimsby Town|
|Derby County v Southampton|
|Accrington Stanley v Ipswich Town|
|Bristol City v Huddersfield Town|
|Wrexham or Newport County v Leicester City|
|Fulham v Oldham Athletic|
|Shrewsbury Town v Stoke City|
|Solihull Moors or Blackpool v Arsenal|
|Manchester City v Rotherham United|
|AFC Bournemouth v Brighton & Hove Albion|
|West Ham United v Birmingham City|
|Woking v Watford|
|Burnley v Barnsley|
|Queens Park Rangers v Leeds United|
|Sheffield United v Barnet|
|Norwich City v POMPEY|
|Guiseley or Fleetwood Town v AFC Wimbledon|
|West Bromwich Albion v Wigan Athletic|
|Middlesbrough v Peterborough United or Bradford City|
|Wolverhampton Wanderers v Liverpool|
|Aston Villa v Swansea City|