Teddy Sheringham returns to Fratton Park tonight.
And Paul Cook has praised the former England international for honing his managerial skills in the lower divisions.
Sheringham lined up for Pompey during the 2003-4 campaign, scoring 10 goals in 38 appearances.
Nowadays he is in the Stevenage hot seat, which represents his first managerial post.
Tonight (7.45pm) will signal a reunion with the club Sheringham also applied to be manager of last summer.
And Cook is looking forward to welcoming a regular opponent as a player.
The easiest part of the game today is sitting in these studios telling everybody how the game should be played, which is the way the game is nowadaysPaul Cook
The Pompey boss said: ‘I played against Teddy quite a bit at different clubs, even back to his Millwall days.
‘He was a fantastic player, wasn’t he?
‘He showed the pace can be in your brain. You can do things before people have even thought about it.
‘It is great to see young managers like him prepared to come in at League Two level and have a go because it is not as easy as people think.
‘The easiest part of the game today is sitting in these studios telling everybody how the game should be played, which is the way the game is nowadays.
‘It’s great to see people like that in the game at clubs like Stevenage. The first thing they have is an aura about them, they command respect and rightly so.
‘In my opinion, we haven’t got enough bright, young English managers and I think it is great to see.’
Stevenage defeated Wycombe 2-1 on Saturday.