Pompey are out to end a five-year winless run in the FA Cup tomorrow when Macclesfield Town come to visit Fratton Park (3pm).
One man who knows all about success in the competition with the Blues, though, is 2008 winner and 2010 runner-up David James.
And while the former England goalkeeper was amazed to hear of the club’s seven-game winless run since 2010 semi-final success over Spurs, fans’ favourite Jamo was able to reflect on happier times when The News got in contact with him this week.
In tomorrow’s Sports Mail big interview, the 45-year-old relives his FA Cup memories, including the career high Wembley triumph over Cardiff.
James, though, is still frustrated by Didier Drogba’s winnner for Chelsea in the 2010 final - the only goal he conceded in general play from five memorable visits to the home of football.
He said: ‘I did not realise until afterwards but that Drogba goal was the only goal I conceded for Portsmouth in general play at Wembley.
‘We had the two semi finals (West Brom 2008, Spurs 2010), the two finals (Cardiff 2008, Chelsea 2010) and the Community Shield (Man United 2008) that we lost on penalties.
‘Afterwards, I was thinking oh why didn’t I just save it!’
JAMES’ FIVE WEMBLEY VISITS WITH POMPEY
West Brom 0-1 Pompey
FA Cup semi-final, April 5, 2008
A second-half goal from Kanu sends Pompey through to a first FA Cup final in 69 years.
The ex-Baggies striker side-foots an easy chance home after former Blues stopper Dean Kiely had denied Milan Baros.
Pompey 1-0 Cardiff
FA Cup final, May 17, 2008
Kanu’s first-half goal wins the Cup for Harry Redknapp’s Pompey in front of a record 89,874-strong Wembley crowd.
The Nigerian is on hand to scramble home the winner eight minutes before half-time after Cardiff keeper Peter Enckelman spills John Utaka’s cross at his feet.
Pompey 0-0 Manchester United (United win 3-1 on penalties)
Community Shield, August 10, 2008
Pompey put up a gallant fight against Premier League and European Cup holders United before losing out in the season’s curtain raiser on penalties.
The Blues fail to score three of their four spot-kicks, with only Jermain Defoe on target, to hand victory to Sir Alex Ferguson’s side.
David James is outstanding in the contest, thwarting dominant United time and time again – only to be beaten in the shootout by Carlos Tevez, Ryan Giggs and Michael Carrick.
Spurs 0-2 Pompey (aet)
FA Cup semi-final, April 11, 2010
Pompey emerge from the wreckage of relegation and financial meltdown to stun Spurs at Wembley and set up an FA Cup final date with Chelsea.
Avram Grant’s side recover from relegation back to the Championship by upsetting overwhelming favourites Spurs with two goals in extra-time.
Frederic Piquionne and a Prince Boateng penalty stun the Londoners, managed by former Blues boss Harry Redknapp.
Chelsea 1-0 Pompey
FA Cup final, May 15, 2010
Pompey threaten one of the biggest upsets in Cup history when they are awarded a second-half penalty against Premier League winners Chelsea with the scores goalless.
But Prince Boateng, on target from 12 yards in the win over Spurs, sees his half-hit penalty saved by Petr Cech.
Minutes later Didier Drogba nets the winner for Chelsea with a precise free-kick on the hour mark.
Frank Lampard follows in Boateng’s footsteps in missing a penalty for Carlo Ancelotti’s side late on.
But it matters little as Chelsea, who strike the woodwork five times in the first half, claim a league and cup double.