Josh Flint had been informed he ‘wasn’t good enough’ to remain at Fratton Park.
Now, some six months later, the versatile midfielder is lined up for his second first-team outing.
The former Crookhorn College pupil will face Oxford United in the Leasing.com Trophy on Tuesday night (7.45pm).
Having marked his Blues debut with a goal in last month’s 3-1 victory over Norwich under-21s in the same competition, it represents another opportunity to impress.
Yet, at the end of last season, Flint was devastated after being told there would be no fresh deal following his academy graduation.
Remarkably, he won a reprieve, earning a contract until January.
And the ex-Fratton End season-ticket holder is fulfilling his footballing dream.
Flint said: 'Around February I broke my arm and returned with a month of the season left.
‘At that point they offered an injury-extension period, basically a few months at the start of the following campaign.
‘They also said: “At the minute, moving forward, we don’t feel you are good enough”.
‘I was devastated, but still had a chance, so in the summer worked as if I was coming back for a new season.
‘I’m a Pompey fan, I wanted to play for them, so had to take the disappointment on the chin and keep working hard.
‘If they were going to keep me around training, I might as well give it my all, perhaps something good could happen. You never know who’s watching.
‘Then I was told I had really impressed and they wanted to keep me around. I was offered another contract.
‘It just shows how quickly things can change in football, you just have to keep working hard, trying to impress.’
Flint represented Widbrook United before signing for Pompey at the age of eight.
The Waterlooville youngster also attended Queens Inclosure Primary School, where his mum, Sam, worked as a teaching assistant.
And growing up, he lists Jed Wallace, Jermain Defoe, Niko Kranjcar and Conor Chaplin as his heroes.
He added: ‘At the start of my scholarship two years ago, I was one of the smallest, I was called ‘short-man syndrome’.
‘Now they call me ‘Lanky’. I’ve grown to 6ft over the last 12 months or so!’