Pompey have been drawn away to Championship side Bristol City in the third round of the Emirates FA Cup.
The tie will take place at Ashton Gate on the weekend of January 9-10.
It will be the first competitive meeting between the sides since they were in the second tier during the 2011/12 campaign, with both contests that season ending goalless.
Pompey were FA Cup holders when they faced the Robins in the same round of the competition back in 2009 and were held to a 0-0 draw on home soil.
But Tony Adams' side got the job done in the replay, with goals from Peter Crouch and Niko Kranjcar securing a 2-0 victory.
There were two other previous FA Cup clashes and both of them required a second game to settle the tie, although Bristol City came out on top in both 1935 and 1973.
"We've had a number of cup games against sides from that division in recent years and enjoyed some memorable wins against Norwich and Barnsley."
Pompey's assistant manager Joe Gallen said: "They're a Championship club and that's a level we're trying to get into ourselves.
"We've had a number of cup games against sides from that division in recent years and enjoyed some memorable wins against Norwich and Barnsley.
"It's a good challenge for us against a team who are doing very well in the league, but we'll be working hard to try to get through to the next round."
Dean Holden's men are currently sitting just inside the Championship play-off places, but were beaten at Reading on Saturday.
Pompey have already played two rounds to get to this stage of the competition, seeing off Ipswich and King's Lynn.
A new date will now have to be found for the Blues' League One clash with AFC Wimbledon that was scheduled for January 9.
|Emirates FA Cup third round draw|
|Huddersfield Town v Plymouth Argyle|
|Southampton v Shrewsbury Town|
|Chorley v Derby County|
|Marine v Tottenham Hotspur|
|Wolverhampton Wanderers v Crystal Palace|
|Stockport County v West Ham United|
|Oldham Athletic v AFC Bournemouth|
|Manchester United v Watford|
|Stevenage v Swansea City|
|Everton v Rotherham United|
|Nottingham Forest v Cardiff City|
|Arsenal v Newcastle United|
|Barnsley v Tranmere Rovers|
|Bristol Rovers v Sheffield United|
|Canvey Island or Boreham Wood v Millwall|
|Blackburn Rovers v Doncaster Rovers|
|Stoke City v Leicester City|
|Wycombe Wanderers v Preston North End|
|Crawley Town v Leeds United|
|Burnley v Milton Keynes Dons|
|Bristol City v POMPEY|
|Queens Park Rangers v Fulham|
|Aston Villa v Liverpool|
|Brentford v Middlesbrough|
|Manchester City v Birmingham City|
|Luton Town v Reading|
|Chelsea v Morecambe|
|Exeter City v Sheffield Wednesday|
|Norwich City v Coventry City|
|Blackpool v West Bromwich Albion|
|Newport County v Brighton & Hove Albion|
|Cheltenham Town v Mansfield Town|