Pompey have not reached the fifth round of the Emirates FA Cup since going all the way to the final in 2010.
Barnsley are standing between Kenny Jackett’s side and a place in the last 16 of the competition this weekend.
The Yorkshire side have not enjoyed much recent success in the competition either – they are on their best run for seven years.
Gerhard Struber’s men earned their trip to Fratton Park with a 3-1 victory at League Two side Crewe three weeks ago.
They are currently involved in a battle to beat the drop from the Championship, although have climbed off the foot of the table in recent weeks.
But the Tykes are still in the bottom three and four points adrift of the safety mark with 17 matches remaining.
The hosts will be wary of Conor Chaplin’s return, with the former Blues favourite having netted nine goals in his past 14 appearances.
It finished 1-0 to the Reds in the only previous FA Cup clash between the sides, which took place all the way back in 1907.
Both of last season’s League One meetings finished all square, with Omar Bogle having a penalty saved in a goalless contest on the south coast.
James Bolton could be fit enough to feature, despite limping off with a thigh injury against Scunthorpe.
But Cameron McGeehan – who opened his Blues account on Tuesday night – is unable to feature against his parent club.
Ross McCrorie has returned to training, but this weekend’s game comes too soon for the versatile loanee.
It leaves Lee Brown (Achilles) and Bryn Morris (groin) as the only members of the squad currently injured.
Barnsley will be without defender Bambo Diaby, who is suspended during an FA investigation, while Mike Bahre is ill.
Clarke Oduor is expected to be fit following an ankle injury and the visitors could hand a debut to new signing Michael Sollbauer.
HEAD TO HEAD
Pompey: 21 wins
Barnsley: 18 wins
At Fratton Park
Pompey: 14 wins
Barnsley: 5 wins
Pompey fans can secure tickets online here or by visiting the Anson Road ticket office.
From 9am on Saturday, they can also be bought from the matchday ticket office in Frogmore Road, which is the location for ticket collections.
Referee: Graham Scott
Assistants: Mark Pottage and Steven Plane
Fourth Official John Busby
Pompey or Barnsley will be ball number 15 in Monday evening’s draw for the fifth. Click here for more details.
Due to engineering works, buses replace trains between Fareham/Havant and Portsmouth stations on Saturday.
Journeys will take longer and be more crowded than usual, so please plan accordingly. Click here for more information.
Overseas subscribers should note that there is no live iFollow video coverage of FA Cup games, although audio commentary will be available.
The match has been selected for overseas broadcast, so supporters outside the UK should check local listings to see if the game is being televised in their region.
ALSO IN EMIRATES FA CUP
Games kick-off at 3pm unless stated
Northampton v Derby (8pm)
QPR v Sheffield Wednesday (8pm)
Brentford v Leicester (12.45pm)
Burnley v Norwich
Coventry v Birmingham
Millwall v Sheffield United
Newcastle v Oxford
Reading v Cardiff
Southampton v Tottenham
West Ham v West Brom
Hull v Chelsea (5.30pm)
Manchester City v Fulham (1pm)
Tranmere v Manchester United
Shrewsbury v Liverpool (5pm)
Bournemouth v Arsenal (8pm)