Pompey take on non-league Macclesfield Town tomorrow looking for their first victory in the FA Cup for over five years.
Paul Cook has promised to play a strong side with loan signing Mark McNulty up for a debut as Sheffield Wednesday have refused to let Caolan Lavery play. Matt Clarke has been given permission to play from Ipswich but is likely to remain on the bench.
Defender Neill Byrne and midfielder Theo Bailey-Jones are injured for Macclesfield but striker Chris Holroyd is likely to start after returning against Braintree last week.
When Kevin Prince-Boateng buried that extra time penalty against Tottenham in the FA Cup semi-final in 2010 nobody sat at Wembley that day thought it would be at least another five years before Pompey would win again in the most famous competition in English football.
Brighton, Chelsea, Notts County, Stevenage and Aldershot have all unceremoniously dumped Portsmouth out of the FA Cup since that 2010 final defeat to Carlo Ancelotti's men but surely that run has to come to an end tomorrow?
The Silkmen lost their last game at Braintree 1-0 in front of a crowd of just 687 people and currently lie 13th in the National League but their form hasn't been too bad with four wins in their last six games. With the crowd set to be at least 12,000 tomorrow the visitors will undoubtedly relish the tie much like the Shots did last season.
Paul Cook's team are undoubtedly better than Andy Awford's mob of last year and he has promised to field a strong team. However, given that Pompey are winless in three games and haven't won at Fratton Park for almost two months then there will always be that niggle of doubt that another frustrating stalemate (or worse) could be on the cards.
Hopefully whoever is picked will do a professional job and see Portsmouth into the second round of the FA Cup since the 80's. The league may be a priority but a good cup run can only boost the confidence and a third round draw against a big club would certainly get people inspired and interested in the competition that Pompey won outright seven years ago.
But a second consecutive defeat to non-league opposition doesn't bare thinking about...
Predicted Starting Line-Ups
GK: Brian MURPHY
RB: Ben DAVIES
CB: Christian BURGESS
CB: Adam WEBSTER
LB: Enda STEVENS
DM: Michael DOYLE
DM: Adam BARTON
RM: Gareth EVANS
AM: Adam McGURK
LM: Kyle BENNETT
CF: Mark McNULTY
Evans might be a good bet to score against his hometown team that gave him his chance in football in what should be a more open game than usual due to the nature of the FA Cup. Macc will have nothing to lose by going for it but Pompey should have too much for them.
Portsmouth 2 Macclesfield Town 1