Pompey head to Ipswich in the FA Cup third round on Saturday.
Here are some memorable moments on their travels in the famous cup competition from more recent times.
Blackburn 3 Pompey 3
January 8, 1994
Alan McLoughlin grabbed a stoppage-time leveller to earn Pompey a third round replay at the Premier League side.
It would also prove to be the only hat-trick of his career as Kenny Dalglish’s in-form side were denied.
Jim Smith’s team fought back three times to ensure Rovers were brought back to Fratton Park, with Alan Shearer, Kevin Gallagher and Tim Sherwood scoring for the hosts.
Middlesbrough 2 Pompey 4
February 26, 1992
Colin Clarke marked a return to the starting line-up with a double as Jim Smith’s side won the fifth round replay.
Darren Anderton also struck twice at Ayresome Park, with Paul Wilkinson responding for the hosts.
Man Utd 0 Pompey 1
March 8, 2008
Manchester United won the Champions League final against Chelsea at the end of the 2007-08 campaign.
But 10 of that side were undone by Pompey two-and-a-half months earlier in the quarter-finals.
Sylvain Distin had produced his memorable tackle on Michael Carrick before Milan Baros was fouled by Tomasz Kuszczak and Sulley Muntari scored from the penalty spot.
Blackburn 1 Pompey 2
January 9, 1988
Pompey were reeling from the sale of Mick Kennedy to Bradford as they headed to Ewood Park in the third round.
Yet Alan Ball’s strugglers responded with victory – Kevin Dillon’s stunning 35-yard volley clinching it.
Led by new skipper Noel Blake, the Blues saw Mick Quinn’s opener cancelled out by Simon Garner – then Dillon got his winner.
Coventry 1 Pompey 2
January 12, 2010
On a bitterly cold night, Aaron Mokoena’s winner in the last minute of extra time gave victory over Coventry.
Avram Grant’s team had to rely on Stephen Wright’s 90th-minute own goal, however, to keep them in it after Leon Best had given the hosts a first-half lead