Danny Cowley has already guided Pompey through to the third round of the Papa Johns Trophy.
And now he is hoping to do the same in the Emirates FA Cup when MK Dons visit Fratton Park on Saturday.
The two League One sides know that victory means a potential clash with one of the big Premier League sides, who all enter Monday’s draw.
Cowley is certainly not underestimating this weekend’s opponents, though, despite their slow start to the campaign.
The Blues boss said: “We’re pleased to have navigated through one cup competition already this week and now we want to navigate through another.
“It would be brilliant to reach the third round – it would be a special occasion to face a Premier League side at Fratton Park.
“But we know that we’ve got to get through a really tough test against MK Dons first and we expect to see the best of them.
“They had a great win in the first round and are a dangerous team who are well coached and have plenty of good players.
“It was an outstanding season for them last term and they probably deserved to be promoted, but just came up short in the play-offs.
“When a team perhaps overachieves, they often lose some of their best players – with the likes of Scott Twine and Harry Darling moving to Championship clubs.
"It would be brilliant to reach the third round – it would be a special occasion to face a Premier League side at Fratton Park."
“They’ve also had some key injuries to deal with, but some of them are starting to come back and you’re now seeing more consistency.
“A lot of teams come to Fratton Park and sit behind the ball – as is their prerogative – but I don’t anticipate MK Dons being like that.
“They have a clear style, like to dominate the ball and ask a lot of questions of you, so we’ll have to be at our best, both in and out of possession.”
Cowley also revealed that the treatment room is beginning to empty, while he is waiting for news on the availability of a couple of loan players.
He said: “We came through clean on Tuesday and everybody who travelled to Ipswich trained on Thursday, while Marlon Pack joined the group.
“Louis Thompson, Michael Jacobs and Tom Lowery are also back on the grass, so things are looking more positive.
“We’ve also been in dialogue with the parent clubs of Dane Scarlett and Owen Dale and we’re hoping they will be available.”
Cowley hopes to go into the tie in a good mood by seeing England win their second World Cup group match this evening.
He said: “We watched the Iran game together before travelling to Ipswich and I didn’t anticipate six goals, while it was a brilliant performance from Jude Bellingham.
“It couldn’t have gone any better and if we can get a positive result against USA, then things are looking bright.”