Bournemouth form the opposition for Paul Cook’s team in a match whose profits are to be allocated to the player who made 361 appearances and scored 68 times for Pompey.
After hanging up his boots, McLoughlin became part of the Blues’ Academy set-up which produced the likes of Jed Wallace, Jack Whatmough, Adam Webster, Conor Chaplin, Ben Close and Brandon Haunstrup.
The former Republic of Ireland international is currently head of Swindon’s under-18s.
But on Saturday he will be among the Fratton end for the occasion to honour his sterling service at the club.
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He said: ‘I have never sat in the Fratton end, although I’ve collected balls from there following shooting practice!
‘I don’t know where exactly I will sit. I’ll find a random seat so I can sample the atmosphere and watch the game from another perspective.
‘I have always been playing, in the dug out or sat in the press box so it will be great to see the match as a fan – which obviously I now am.
‘It is something I have always wanted to do.
‘Considering the amount of games I have played at Fratton Park, particularly after the new stand was built, the Fratton end has always seemed an exciting place.
‘When the fans are behind the team it is a hell of a place, the noise levels which come from it and the amount of people packed in there is fantastic.
‘I was playing in the Stockport game – what a memory that continues to be.
‘I have also tucked many a penalty into that goal, so it holds happy memories.
‘It will be a random spot, not too far up with my legs and I’m looking forward to it.’