He was once a teenager in a Pompey squad which experienced the most calamitous pre-season tour of them all.
Now Perry Ryan will be going head to head with the latest crop of Blues youngsters hurled in at the deep end to cover player shortages.
And the versatile Hawks performer is relishing the opportunity to face the club where he spent 11 years.
It was back in the summer of 2010 when Ryan was among nine promising players pushed into the first-team environment by then-manager Steve Cotterill.
The Copnor youngster went on to make five appearances, most of them coming on Pompey’s infamous tour to America and Canada that year.
During that time, Ryan was part of the side which lifted the Edmonton Cup, although come the season’s end he was released along with Billy Goddard, Ellis Martin, Tom Kilbey, Peter Gregory and Marlon Pack.
Ryan was subsequently snapped up by then Hawks boss Shaun Gale, making 36 appearances last term at Westleigh Park and scoring three goals.
Nowadays converted from a central defender into a central midfielder, the 20-year-old will be part of Stuart Ritchie’s squad which will take on Pompey in a friendly this afternoon (3pm).
Some of those making up the opposition will be players he trained alongside at Pompey’s Eastleigh base just over a year ago.
And Ryan – who is one of four ex-Blues players in the Hawks squad – is eager for the opportunity to lock horns with his home-town club.
He said: ‘It was fantastic being part of that pre-season. I certainly remember Steve Cotterill!
‘To be honest, there were a lot of us youngsters in the squad but we were not ready for the team. I have since come to terms with that.
‘The travelling on the tour to America and Canada was terrible. We had so many flights. One time we had to get up in Chicago at 4am to get a 7pm flight. It was ridiculous.
‘Then there was the Edmonton Cup. I came on as sub and nearly scored at the back post in the 90th minute.
‘That might have changed my fortunes if that had gone in!
‘I never made it into the first team after that summer but it was still great being around those senior players.
‘There I was along with Ellis Martin and Billy Goddard – lads I had played with since I can remember – and we were training alongside people like David Nugent and Richard Hughes, smashing guys who were so kind.
‘Also among our group was Tom Kilbey – what a character!
‘He’s got talent but has gone into a television programme (The Only One Is Essex) with made-up stories and chosen to live in a fantasy world!
‘I was there at the club for the rest of the season and would train with the first team.
‘All of them, apart from Tal Ben Haim, were brilliant. People like Liam Lawrence and Hayden Mullins would pull me aside to give advice, which was really appreciated.
‘I’m 20 now and, fingers crossed, will be back there one day. Jason Pearce showed it can be done.’
Ryan’s versatility has seen him operate for the Hawks as a central defender, left-back and right-back.
Yet it is the centre of midfield which has become his preferred position.
Regardless of where he features today, though, Ryan is just eager to face Pompey in a match that is likely to see the Hawks unveil a new striker.
He added: ‘I will be looking forward to seeing what team Pompey put out, to be honest.
‘We have been back training for two weeks now and are looking stronger and fitter than last season.
‘It will be a tough test for Pompey.We are hungry and a few of us are clearly out to prove a point.
‘It’s funny, I was with Pompey from the age of eight after being brought to the club by Dave Hurst and Sean North and played centre half for all that time.
‘Now I’m a central midfielder!’