Seeing Matt Ritchie score a crucial goal against his hometown club for Swindon was enough to pain Pompey supporters on Tuesday.
But there is still space for quiet satisfaction for the coaches who help develop the careers of local youngsters like the Gosport talent.
Ritchie’s face didn’t fit under Steve Cotterill at Fratton Park, paving the way for his move to the County Ground last year.
League Two player of the year plaudits have followed as the 23-year-old helped his side to the title last season.
Although there is an element of frustration that Ritchie didn’t make the grade at the club he loves, Pompey Academy head of coaching Paul Hardyman believes there can still be pleasure at seeing Ritchie have a career in the game.
He feels the attacking talent – and plenty of others who came through the ranks with when he was a player at Fratton Park – offer a lesson to those trying to make it now.
‘When you see players like Matt Ritchie do well it is the type of thing you get a buzz from as a coach,’ said Hardyman.
‘Obviously, we wanted to see him come through and do that at Portsmouth.
‘But I’d never criticise a manager because they have to make the decisions they live or die by.
‘Matt will not be the first or last player who leaves Portsmouth and goes on to have a good career elsewhere.
‘There are three players I talk about when I was in the first team who didn’t get contracts.
‘Liam Daish, Brett Angell and Steve Claridge were all released on free transfers.
‘But they all ended up being £1m players and going on to have careers in the Premier League.
‘Decisions had to be made with them, but they all went on to become good players and have good careers.
‘That is a message to the players here now.
‘It’s about the production of players at Portsmouth who go on to have a career in the game.’
The Academy return to league action after a free weekend with a trip to Southend on Saturday.
It’s been a mixed bag when it comes to results, with the under-18 side picking up two wins, two defeats and a draw to date.
Hardyman has been largely happy with what has been produced in terms of performance, however.
He said: ‘The performances have been good.
‘We lost 3-1 to Bournemouth in our last match and we had 75-per-cent possession and created 22 chances in the game.
‘It was one of those days where we could have played for another 90 minutes and not scored.
‘But, overall, we’ve been happy with what we’ve seen so far.’