Between them, Jamal Lowe and Conor Chaplin plundered more than half a century of goals during their Fratton Park days and were part of the League Two title-winning team.
Now the duo are going head-to-head for a Wembley spot in the hunt to reach the Premier League.
Swansea boast a 1-0 advantage ahead of tonight’s semi-final second-leg clash with Barnsley (6.30pm).
Lowe featured for the full 90 minutes of Monday’s first-leg at Oakwell as Andre Ayew handed Steve Cooper’s side a slender lead.
He has netted 14 times in the Championship this season after arriving in a cut-price move from cash-strapped Wigan in August.
Now aged 26, he registered 29 goals in 119 Blues outings before departing for the Latics in August 2019 for a fee of around £2m.
Meanwhile, Chaplin is in Barnsley’s squad for this evening’s decisive fixture.
Although not called upon from the bench for their first-leg, he has featured 39 times for the Tykes in all competitions this term.
However, he has been unable to match last season’s goal haul of 13, registering just four so far this season.
Nonetheless, he has been a regular starter for Barnsley and will be pushing for a starting spot in the Liberty Stadium fixture.
And Pompey fans will no doubt be wishing Chaplin well, having netted 25 goals in 122 appearances for the Blues after emerging from the Academy.
Meanwhile, Swansea have another name familiar to the Fratton faithful in Wayne Routledge.
Now aged 36, the midfielder was part of the Great Escape side under Harry Redknapp in the 2005-06 campaign.
Routledge featured 13 times during a loan spell from Spurs as the Blues preserved their Premier League status.
He has since played for Fulham Villa, Cardiff, QPR (twice), Newcastle and Swansea.
Routledge, who came off the bench in the first-leg, has totalled 304 appearances and 33 goals since joining the Swans in August 2011.
A message from the Editor, Mark Waldron
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