Pompey will travel to Ipswich in the third round of this season’s FA Cup.
The Blues met the Tractor Boys at the same stage of the competition back in 2008 – the year Sol Campbell lifted the Cup for Harry Redknapp’s side.
But this is the first time Pompey have reached this far in the competition since a 4-0 defeat at Chelsea in 2012.
Here’s how they have fared in the third round since that memorable Wembley day in 2008.
Chelsea 4-0 Pompey
January 8, 2012.
In a rematch of the 2010 final, Pompey were well-beaten by Chelsea.
Michael Appleton’s side kept them out until half-time, but a Juan Mata goal on 48 minutes broke the resistance and the hosts ran out comfortable winners.
Brighton 3-1 Pompey
January 8, 2011.
The Blues played 76 minutes with 10 men, after Dave Kitson was sent off for an elbow on Adam El-Abd, enabling the League One leaders to lead 2-0 at half-time.
Substitute Tom Kilbey pulled one back, but Brighton grabbed a stoppage-time third to progress.
Coventry 1-2 Pompey (Replay, AET). January 12, 2010.
Leon Best had seemingly sent Coventry into the fourth round at the Ricoh Stadium, but Stephen Wright’s last-gasp own goal took the tie into extra-time.
It was left for Aaron Mokoena to head home a 121st-minute winner in a journey which would lead to the FA Cup final.
Bristol City 0-2 Pompey (Replay)
January 13, 2009
A goal in each half from Peter Crouch and Niko Kranjcar helped FA Cup holders Pompey overcome a tricky replay at Bristol City.
Yet it was David James who shone, saving a Nicky Maynard penalty and producing several superb stops to ensure the visitors triumphed under Tony Adams.
Ipswich Town 0-1 Pompey January 5, 2008
Substitute David Nugent was the match-winner against an Ipswich side reduced to 10-men following Liam Trotter’s sending off.
Nugent had been struggling to live up to his £6m price tag, but enabled Harry Redknapp’s side to progress in a season which would ultimately lead to Wembley glory.
– MATT STOREY