The EFL Trophy – in any of its various guises – has never been successfully defended.
So Joe Gallen hopes that Pompey can make history by lifting the silverware for a second consecutive season.
They beat Sunderland in front of a record attendance at Wembley last March and have progressed to the third round this term.
It means that a place in the final eight is at stake when the Blues pay a visit to League Two outfit Walsall.
And Gallen hopes their impressive form in the competition will continue at the Bescot Stadium this evening.
Pompey’s assistant manager said: “We’ve always treated the Leasing.com Trophy with a lot of respect and we want to get through to next round.
“If we do that then we’re in the quarter-finals, so it will be a strong team because we want to go all the way again.
"The side will be full of first team players, although there might be some freshening up from the team that played Fleetwood."
“We understand it’s going to be a tough place to go and get a result, so will have to play well if we’re going to win.
“The side will be full of first team players, although there might be some freshening up from the team that played Fleetwood.
“We’re looking forward to the tie and it’s important that we enjoy it, while looking to produce the performance that’s required.”
The January transfer window has only been open for a week, but Pompey have already added Steve Seddon and Reeco Hackett-Fairchild to their ranks.
Gallen said: “As soon as one window closes, you immediately start to work on the next one, although it’s not always easy to sign players – especially in January.
“But I think it’s fair to say that we’re looking to improve the squad where we can in the few weeks ahead.
“Reeco has done well for Bromley and scored a few goals for them this season, mainly playing on the left-hand side.
“He’s had a good upbringing in football and we’re excited about him because there’s a lot of potential.
“We were pleased to bring Steve in last week. He’s another one with a good grounding in the game and did particularly well in this league with Wimbledon last season.”