Kyle Bennett insists Paul Cook’s experience and knowledge of League One can help Pompey secure back-to-back promotions.
And the winger believes the Blues proved their doubters wrong when they clinched the League Two title.
Cook’s men won the championship on the final game of the season after dispatching Cheltenham 6-1 at Fratton Park.
It was the second time the Pompey manager had scooped the League Two crown in his career.
Cook guided Chesterfield to success three years ago.
He then stewarded the Spireites to a sixth-place finish in the third tier in the 2014-15 season.
But Chesterfield were beaten in the play-off semi-finals by Preston.
Bookies have made the Blues second favourites for the League One title next season.
Meanwhile, Bennett feels Cook is in a stronger position to go up with Pompey than he was when in the Chesterfield hot seat.
The former Doncaster Rovers winger said: ‘Teams coming from League Two into League One and going straight up again has happened before.
‘The gaffer almost did it at Chesterfield previously.
‘He got them in the play-offs but didn’t quite manage to make it.
‘But I don’t think they had the resources and the players we have got here.
‘The main goal for us is promotion next season.
‘Hopefully, we can get into a similar situation (as Chesterfield) and get over the line. It wouldn’t be a surprise for us to do it.
‘Given the size of the club, why not have the aspirations to do it again?’
Bennett was an influential member of Pompey’s success this season.
He was rewarded with a new three-year deal – keeping him at Fratton Park until 2020 – on Tuesday.
The 26-year-old particularly enjoyed the second half of the campaign, scoring four goals in as many matches against Crawley, Colchester, Grimsby and Newport County.
It was Pompey’s form in the closing stages that ensured they landed the League Two title.
They registered 10 wins and one draw and pipped Plymouth Argyle to the silverware on the final day.
Bennett revealed he and his team-mates saw the light at the end of the tunnel and put everything into their title challenge.
He added: ‘The second half of the season was good and everyone picked up.
‘Everyone laid their cards on the table and we just went for it and managed to get over the line.
‘Nobody expected us to win the title.
‘Every game we got a bit closer but it didn’t seem realistic.
‘If you were putting your mortgage on a team to win the league, you wouldn’t have put it on us.
‘For us to do it was brilliant.’