Pompey have enjoyed plenty of success in the EFL Trophy in recent years.
They beat Sunderland on penalties at a packed Wembley in 2019 and are still waiting to face Salford in last season’s final.
In fact, you have to go back two years and nine months to find the last time they lost in the competition.
And the Blues know that victory in this evening’s Southern Group A contest at Southend would see them progress to this term’s knockout stages with a game to spare.
Even a draw would be enough to qualify should they win the resulting penalty shoot-out and claim a bonus point.
Their opponents were relegated from League One last season, with ex-Fratton coach Kevin Bond replaced as manager midway through by Pompey’s FA Cup-winning skipper Sol Campbell.
He departed following their fall into the basement, with Mark Molesley leaving Weymouth to take charge at Roots Hall.
The Shrimpers have had a difficult start to the current campaign, although did collect their first point in Saturday’s 1-1 stalemate at Crawley.
Pompey fans might still be having nightmares about the last clash between the sides in Essex, when they let slip a three-goal lead to draw 3-3 in February 2019.
They also met at Roots Hall in the EFL Trophy the previous month, when goals from Louis Dennis and Gareth Evans secured a comfortable 2-0 victory for the Blues.
Pompey have no injury concerns, but are likely to make several changes from the side that won at Burton in the league on Saturday.
Alex Bass will replace Craig MacGillivray between the sticks, while on-loan Danish defender Rasmus Nicolaisen is in line to make his debut.
Southend will be missing right-back Elvis Bwomono, who has been called up for international duty with Uganda.
VIEW FROM THE DRESSING ROOM
Read the thoughts of Joe Gallen ahead of this evening’s game.
HEAD TO HEAD
Pompey: 19 wins
Southend: 11 wins
Pompey: 5 wins
Southend: 9 wins
Referee: Paul Howard
Assistants: Stephen Finch and Scott Williams
Fourth Official: Andy Bennett
Supporters can watch the action live (please note coverage will be provided by a single camera) by purchasing a match pass for £10.
Please note that subscribers based in the UK and Ireland will still need to purchase a match pass in order to watch the game live.
ALSO IN EFL TROPHY
Games kick-off at 7.45pm unless stated
Shrewsbury v Bolton (5.30pm)
Stevenage v MK Dons (5.30pm)
Peterborough v Fulham U21 (6pm)
Accrington v Blackpool (7pm)
Burton v Cambridge (7pm)
Forest Green v West Brom U21 (7pm)
Ipswich v Gillingham (7pm)
Leyton Orient v AFC Wimbledon (7pm)
Mansfield v Lincoln (7pm)
Newport v Norwich U21 (7pm)
Oxford v Bristol Rovers (7pm)
Sunderland v Carlisle (7pm)
Swindon v Exeter (7pm)
Wigan v Port Vale (7pm)
Bradford v Wolves U21 (7.30pm)
Northampton v Southampton U21 (7.30pm)
Cheltenham v Plymouth
Fleetwood v Aston Villa U21
Harrogate v Leicester U21
Oldham v Doncaster
LAST EFL TROPHY MEETING