As a lad he journeyed from the Isle of Wight to cheer on Pompey.
Now Gary Rowett is plotting their second successive League Two defeat.
The 40-year-old’s Burton Albion side are top of the table and undefeated in seven matches in all competitions this season.
Having lost out in the previous two play-offs, the Brewers are focused on securing promotion automatically.
For Rowett, Sunday’s fixture pits him against a team he used to follow.
Despite being an Everton fan born in Bromsgrove, the former Derby defender grew up on the Isle of Wight.
And he ventured to the mainland to take in Pompey’s progress during his younger years.
Nowadays Rowett is excelling as boss of the Brewers and seeking a positive result against the Blues on Sunday (12.15pm).
He said: ‘Pompey have improved since last year and have got a little bit of stability now that Andy’s the manager.
‘He knows the club inside out, he’s been there a long time and has been a huge part in their history.
‘That’s important because someone who takes over them needs to understand what the club’s about and what it means to the fans.
‘They’re the club I used to go and watch games at when I lived on the Isle of Wight.
‘I know a little bit about the club and how fervent the fans are and what a brilliant fanbase they’ve got.
‘It’s going to be a difficult game. They were one of the most fancied teams for promotion at the start of the season.
‘Whether that’s due to their size, you can make an argument, or whether it’s down to the players they’ve brought in, but I expect them to be there or thereabouts.
‘It’ll be a different test and I think every game so far has been a different test.
‘Will it be harder than playing QPR? Will it be harder than playing Wigan? Will it be harder than playing the first 45 minutes against Dagenham? I don’t know.
‘But what we do know is it’ll be a different test and one which we’ll have to be very, very well prepared for and will have to start the game brightly.’
Pompey won their visit to the Pirelli Stadium last season under Guy Whittingham.
Ricky Holmes and Simon Ferry both scored in a 2-1 victory for the visiting side, despite having Yassin Moutaouakil sent off late on.
John Sullivan was beaten in stoppage time during a nerve-racking finale, but the Blues held on to win.