Accrington was his first Football League club, Pompey his maiden opposition.
Now Kal Naismith heads back to the Crown Ground for the first time since his summer departure.
And with only a point separating the sides in the battle for promotion, the fixture’s importance cannot be underestimated.
It was August 2013 when Naismith arrived at Stanley from Glasgow Rangers and was swiftly granted a debut in the televised visit of Guy Whittingham’s Blues.
The match finished 2-2, the winger lasting the full duration as the hosts snatched an 85th equaliser through Peter Murphy.
He went on to total 79 games, scoring 14 goals, before moving to Fratton Park for an undisclosed fee in May 2015.
Naismith still possess plenty of friends at his former club – while manager John Coleman has his admiration.
Yet Pompey urgently require a positive result in tonight’s (7.45pm) clash between League Two’s fourth and five-placed clubs.
He said: ‘My debut was against Pompey on a Saturday on Sky. The sun was there and I thought “This is great”.
‘Then the league got tougher and the pitches got worse! But I loved my time at Accrington and am grateful to them.
‘James Beattie brought me to the club, with John Coleman taking over last year and he has done a tremendous job, his players have been excellent.
‘They are certainly a lot higher in the league, maybe that is because I have now gone!
‘He demands a lot from his team and I guess everyone has their different opinions of managers, but he was always really good with me. A great man first and foremost.
‘There are no egos in that dressing room, they just get their heads down and work hard. I guess that is showing this year where they are in the league.
‘Their players have been excellent and let’s hope tonight those normally doing so well have an off-day. This is a big game, just like they all are in a run-in.
‘We know it is a tough league and if anyone can put a run together you can certainly get yourself up there.
‘Accrington, with the greatest of respect, are a small club and to be where they are this year is great.
‘But we have to concentrate on ourselves and do what we do best – hopefully getting the three points.’
Accrington are currently one place and one point above the Blues, with a game in hand.
Paul Cook’s side certainly cannot afford a defeat at the Crown Ground in a fixture rearranged from January.
Stanley, however, will be without Naismith’s former team-mate Josh Windass through injury.
The attacking midfielder and Matt Crooks signed a pre-contract agreement with Scottish giants Rangers in January ahead of a summer switch.
Naismith added: ‘It just shows you big clubs like that are looking at Accrington players now – you wouldn’t have thought that would have happened before.
‘Credit to Josh and Matt, they are both every good players and will certainly fit in there, hopefully they can do well.’