Kenny Jackett will draw on the experience of his FA Cup achievement with Millwall as he looks to guide Pompey to another memorable run in the competition.
The Blues boss was in charge at the Den when the London side reached the last four in 2013.
His team were eventually knocked out by Wigan Athletic who famously went on to beat Manchester City and lift the Cup.
Despite missing out on the final it was a campaign to remember for the Lions.
Now Jackett hopes he can use those experiences to take League One leaders Pompey on a good run.
He said: ‘We lost to the eventual winners.
‘Wigan beat Manchester City 2-0 in the final and we lost to them.
‘It was a Wembley appearance and it was great for us to get that far.
‘We were really hoping to get through to the final, it was disappointing to lose at that late stage.
‘But as a Championship club, as we were at that particular time, to get through to the semi-final was a great achievement.
‘It did us all the world of good and we’ll try to do that again.’
The Blues face National League strugglers Maidenhead United in the first-round tie in front of the BT Sport cameras tomorrow (12.30pm).
Jackett has stressed Pompey’s push to reach the Championship is the priority this season.
However, he believes that can marry up nicely with a good run in the Cup.
The Blues boss added: ‘It's a terrific competition and it’s one we want to do well in.
‘There are many advantages to it.
‘It’s a good experience for the players, exciting for the supporters winning in the Cup and then the anticipation of who you can draw and how far you can go.
‘Also the overall picture of potential finance for the club, which can impact on our season and seasons ahead.
‘There are many reasons why we want to do well in this competition.
‘To do that we have to come through very difficult and tricky ties like this.
‘It will be the same this weekend.
‘I always take it seriously, we'll be doing everything we can to prepare.
‘We'll prepare as we would for a league game and, if possible, we can settle the side down and get into a rhythm.
‘We want to continue our good form.’