Pompey have an FA Cup pedigree that would be the envy of many other clubs.
The two-time winners have lifted the trophy at Wembley and finished as runners-up within the past decade.
But their fall down the divisiosn has also resulted in some less glamorous outcomes, with a first round exit to Aldershot in 2014 immediately springing to mind.
Now Pompey prepare for their latest campaign in the world’s most popular domestic cup tournament.
And Kenny Jackett is hoping for a first round victory at Luton to spark an upturn in form following three successive league losses.
The Blues boss said: “It’s a great competition, but you’re always looking for a home game if possible and so it’s a tough draw for us.
“To have a cup run this season would be fantastic and I know we’ll be well backed by our supporters, who will go there with optimism.
"Our next two games are both in cup competitions and if you win them then it can breed confidence."
“We want to reward them and their loyalty with a good performance and, of course, a good result.
“In the past few years this club has won the FA Cup and also had some first round exits, but hopefully we can do well.
“Our next two games are both in cup competitions and if you win them then it can breed confidence and help improve the team.”
Pompey face a Luton outfit who were sitting at the fourth tier summit, only for last weekend’s home defeat to Coventry to push them down to third.
Jackett said: “Both sides know a lot about each other after competing in the same division last season and Luton are now one of the fancied clubs in League Two.
“They were not too far away last time out and I’m sure they’ll be pushing for one of those promotion places this time around.
“Luton have got a bit of momentum behind them and quite a big squad to play with, but we’re determined to do well.
“It looks like the two teams are evenly matched, although we don’t have home advantage. I’m sure it will be a competitive encounter.”
Pompey will wait and see whether Oliver Hawkins recovers from an ankle problem suffered in training, but the treatment room is starting to empty.
Jackett said: “We’re pretty much clear of injuries now, except for Jack Whatmough and Damien McCrory, who’s had a reoccurrence of his knee injury and has gone back to Burton for them to assess that.
“Adam May is back in training and so is Curtis Main, although Saturday will probably come too soon for him.”