Pompey hold plenty of cup pedigree, having lifted the trophy at Wembley in both 1939 and 2008.
But since reaching the final for a fifth time back in 2010, their record in the competition has been pretty dire.
In fact, the Blues have fallen at the first hurdle on every occasion, except for when Paul Cook led them to the fourth round in 2015/16.
So Ben Close is certainly not harbouring a complacent attitude ahead of Pompey’s trip to National League side Maidenhead on Saturday.
The midfielder said: “It’s a good opportunity for us to produce a decent performance and get through to the next stage of the competition.
“But we know it’s not going to be an easy one and Maidenhead will raise their game, so we have to be professional to get the job done.
"I was at the final in 2008 as a fan and have great memories from that season – now we’re desperate for another cup run."
“We’re a club at the top of League One, so it’s a big match and I don’t think their recent league form will count for much on the day.
“I was at the final in 2008 as a fan and have great memories from that season – now we’re desperate for another cup run.
“Our aim is to get off to a good start on Saturday and hopefully that will lead on to a decent spell for us.”
Close was in the Pompey squad that were embarrassed by non-league Aldershot in a first round replay four years ago.
He said: “I came on in the first game and made a mistake for their second goal, but thankfully Danny Hollands dug me out by getting a late equaliser.
“The replay was pretty frustrating and it was always going to be tough once we fell behind, so we’re well aware that we can’t take Maidenhead lightly.”