Alan Knight was a triumphant manager on his previous visit to York Road.
Now the goalkeeping legend returns to the home of Maidenhead keen to watch Pompey’s FA Cup progress.
It was December 2011 when the newly-appointed Dorchester boss was handed his maiden fixture at the Berkshire-based Magpies.
The outcome in the Blue Square Bet South encounter was a 1-0 success for Knight, Rico Wilson the matchwinner in front of a 269 crowd.
Knight, who took over a Dorchester side in 11th spot, departed at the season’s end in April 2012 due to work commitments, having finished in the same position.
And on Saturday he will return to Maidenhead’s home, albeit this time in his customary role as Express FM summariser.
He said: ‘It was York Road where I made my managerial debut while at Dorchester.
‘Maidenhead weren’t a bad side at the time, the ground was a little bit basic, with parking horrendous, but we finished 1-0 winners so were happy with that.
‘I had been goalkeeping coach with the Hawks at the time and went for the job after Ashley Vickers had left.
‘Before then I had a joint-manager stint with Dave Carter at Horndean for a few months, before working with Kevin Dillon at Aldershot, so had dipped my toe in the water.
‘But at Dorchester I was in charge and went into a club which, in fairness, was in a decent way despite being managerless.
‘There was no magic wand in my possession, but I kept it going and didn’t change it too much. We had a pretty successful season and finished just outside the play-offs.
‘I left at the end of that season because I had to work for a living and the Dorchester job would have clashed with that. I couldn’t give it the full commitment required.
‘I’m looking forward to going back.’
Knight was also present in November 2014 when Pompey suffered a first competitive defeat to non-league opposition in the club’s history.
That was inflicted at Aldershot, courtesy of a 1-0 scoreline in a midweek first-round replay.
And the Blues will be eager to avoid a repeat in front of the BT Sport cameras on Saturday.
He added: ‘The team’s performance was not one of the best, Aldershot deserved to win on the night. They were worthy winners.
‘Sometimes you cannot let your standards drop because they will smell blood. You've got to be ruthless, if you drop down a few gears you will get your bottom smacked.
‘You cannot treat matches like this lightly, the opposition will always raise their game – and you have to be respectful.’