We recall some previous FA Cup clashes
The FA Cup really gets going once the Christmas and New Year festivities are out of the way.
But it is a party that Pompey have not been invited to in the past few seasons.
They have not joined the Premier League and Championship sides in the hat for the third round draw since being relegated from the second tier in 2012.
Victories over Macclesfield and Accrington this season, however, have seen them return to the top table.
And ahead of Saturday’s trip to promotion-chasing Ipswich, we take a look back at Pompey’s most recent third round clashes…
Chelsea 4 (Mata, Ramires 2, Lampard)
Pompey were heading towards a second administration and relegation in the space of just three seasons.
But Michael Appleton’s side put up a brave fight against the side that would go on to lift the trophy at Wembley a few months later.
They went close to taking an early lead at Stamford Bridge when Dave Kitson flashed a shot inches past the post, before Aaron Mokoena sent a header wide.
Instead the hosts broke the deadlock two minutes into the second half, with Juan Mata turning home Florent Malouda’s low cross.
That only seemed to galvanise the Blues, however, and Chelsea survived a scramble in their box, while Petr Cech twice denied Marko Futacs.
But Ramires added a late brace and Frank Lampard drove home a fourth goal to ensure a final scoreline that did not tell the full tale of the tie.
Brighton 3 (Wood, Barnes (pen), Sandaza)
Pompey 1 (Kilbey)
Pompey had roared to the final the previous year, but were undone by League One leaders Brighton at the Withdean Stadium.
Their cause was not helped by Dave Kitson getting sent off for an elbow on Adam El-Abd after just 14 minutes.
And the hosts soon made their numerical advantage count when Chris Wood fired home after Mauricio Tarrico’s effort was deflected into his path.
Ibrahima Sonko then needlessly handled in the box and Ashley Barnes stepped up to convert the spot-kick.
There was hope for Steve Cotterill’s side when substitute Tom Kilbey netted his first – and only – goal for the club, but Francisco Sandaza soon extinguished that with a cool finish.
Pompey 1 (Boateng)
Coventry 1 (Bell)
Coventry 1 (Best)
Pompey 2 (Wright (og), Mokoena)
After Extra Time
Not many people would have predicted a run to the final after Pompey – whose players had yet to be paid their December wages – struggled to see off Championship side Coventry.
The sides draw 1-1 at Fratton Park, with Kevin-Prince Boateng heading home Richard Hughes’ cross to cancel out David Bell’s opener.
And it looked like they were heading out after trailing to Leon Best’s fine goal for the Championship side in the Ricoh Arena replay.
But, in the final minute of the 90, Stephen Wright inadvertently headed the ball into his own net to take the tie into extra-time.
A penalty shoot-out looked to be in the cards, only for Aaron Mokoena to prove an unlikely hero in the dying seconds by glancing home a header.
Avram Grant’s side went on to beat Sunderland, Southampton, Birmingham and Tottenham before losing 1-0 to Chelsea in the final.
Bristol City 0
Bristol City 0
Pompey 2 (Crouch, Kranjcar)
Pompey made a stuttering start to their defence of the FA Cup, as they struggled to see off Championship opposition.
They created the better openings in the first clash at Fratton Park, with Marc Wilson’s effort cleared from the line and Niko Kranjcar heading wide when it appeared easier to score.
But it took an Ashton Gate replay for them to finally get the job done – although Bristol City did not appear over-awed.
David James made a string of fine saves to keep the hosts at bay, including a brilliant stop to keep out Nicky Maynard’s late penalty.
But the Blues also looked dangerous and Peter Crouch finished off a fine counter-attacking move before Kranjcar added a second from close range.
Pompey did fall to second tier challengers at the next stage, however, with Swansea winning 2-0 at Fratton Park.
Pompey 1 (Nugent)
There were certainly more memorable games in Pompey’s quest to win the FA Cup for the first time in 69 years.
But – despite having the best away record in the Premier at the time – they were made to work hard for a third round win at Championship side Ipswich.
And the hosts had to play a large chunk of the tie with only 10 men after midfielder Liam Trotter was sent off midway through the first half for a lunge on Pedro Mendes.
Hermann Hreidarsson and Kanu both missed opportunities to break the deadlock, but a Blues winner did arrive after the restart.
David Nugent neatly controlled a long ball out of defence by Sol Campbell and coolly slotted home his first goal for more than three months.
Pompey went on to beat Plymouth, Preston, Manchester United, West Brom and Cardiff before ‘Sol went up to lift the FA Cup’.