Matty Kennedy admitted it’s ‘make of break’ for Pompey if they are to finish in the League One play-off places.
The Cardiff loanee believes the Blues’ two upcoming away trips could determine their ambitions of making the top six.
Kenny Jackett’s troops sit four points adrift of the play-offs with 14 games remaining this campaign.
Pompey travel to in-form Southend tomorrow, before making the long trip to Fleetwood on Tuesday night.
Having picked up just one victory this year, the Blues cannot afford to lose any more ground on their top-six rivals.
Kennedy believes Pompey are at the most crucial stage of the campaign to date.
And he insisted his side will know if they can finish in the top six come full-time at Fleetwood.
Speaking at a meet and greet event at Covers Merchants & Timber, the winger said: ‘I think right now is probably the most key moment of our season so far.
‘It’s basically crunch time for us.
‘The next few games are going to be make or break for us if we want to make the play-offs.
‘Afterwards, we will know then if we have a good chance of making it (the play-offs) or if we won’t.
‘The next few games coming up are definitely key.
‘At the club we have got a good manager, a good fan base and good fans.
‘So you never know what might happen.’
Kennedy’s contract at Cardiff expires at the end of the season.
His current Pompey loan deal also comes to a close in the summer.
However, there’s a clause in his Blues contract to make a permanent switch to Fratton Park if an agreement can be agreed.
With Cardiff pushing for promotion in to the Premier League, Kennedy admits his game-time might be limited if he was offered a new deal at the south Wales club and returned.
He joked he’ll sign a long-term contract at Pompey if best-mate Dion Donohue is offered the same.
‘Obviously, I’d like to be at Cardiff playing in the Premier League (potentially),’ Kennedy added.
‘However, do I want to go back there, sit on the bench and maybe get the odd game here and there?
‘Or do I drop down a couple of divisions, like in League One with Portsmouth – we might get promoted, you never know – and get more game-time.
‘If Dion signs a five-year contract, then I will as well – he’s my boy!’
– WILL ROONEY