Alan McLoughlin represented Pompey 361 times and scored 68 goals.
On Saturday, the Blues face Bournemouth in a benefit match for their popular former midfielder.
Here are Macca’s five favourite matches during almost eight years at Fratton Park.
February 29, 1992
Pompey 2 Tranmere 0
My Pompey debut saw me face Tranmere at Fratton Park – yet because I had arrived from Southampton there was booing.
Then I put one in the top corner on 11 minutes and suddenly there was no booing.
The match finished 2-0 and I also had a hand in Chris Burns’ goal.
January 8, 1994
Blackburn 3 Pompey 3
This FA Cup match means so much to me as I scored the only hat-trick of my career.
It came against a big-spending Blackburn who would finish runners-up in the Premier League that season, although we lost the replay at Fratton Park.
March 7, 1992
Pompey 1 Nottingham Forest 0
I had been at Fratton Park for two weeks and we had reached the semi-final of the FA Cup after I scored against Nottingham Forest.
Brian Clough’s side were in the top flight and put us under all sorts of pressure as the game wore on, but we stood firm to claim a fantastic win.
February 17, 1998
Pompey 1 Stockport 0
The atmosphere was ridiculous. There were 8,622 supporters present and there is no way you could not be energised by the atmosphere they provided.
We went on to stay up that season and that day will live long in the memory. If you were part of that crowd you should be proud of yourself.
October 15, 1994
Pompey 4 Swindon 3
I had gone 15 games without a goal and we faced my former club with my wife and in-laws, Swindon people, among the crowd.
My daughters, who went to school in Swindon, had been hearing kids saying ‘He’s no good’ – but I scored two goals, both of them headers. My wife had also put £10 on at 8-1 for me to be the first scorer!