The Pompey pair were promising Academy products the last time Ryan Bird encountered them.
Now Jack Whatmough and Ben Close are regular components of a League One table-topping side who could line-up up against the former Blues striker on Saturday.
Whatmough made his debut against Southend in November 2013 – a League Two match in which Bird appeared from the bench.
As for Close, he was a highly-regarded midfielder from the youth set-up, occasionally challenged to train with the first-teamers.
Both have blossomed since Bird’s September 2014 departure from Fratton Park in a career which has now brought him to Maidenhead.
And the striker is intrigued to see the pair in action for the FA Cup first-round clash at the York Road home of the non-leaguers.
Bird said: ‘It will be good to see what Pompey are like, although obviously they are flying now, top of League One and a good team on the way back up.
‘I can’t wait to see Whatmough, we were team-mates and he was 17 when I was there – and good then.
‘I thought “This geeza’s going to be decent”, but Jack had quite a few injuries. It's good to see him come through that, with the club sticking by him, and he’s now playing.
‘Aged 17 he was one of the best defenders there, real quality, quite big for someone of that age as well, while really good on the ball for a defender. He had good attributes to go far.
‘Ben was more in the youth team and you could see his talent as well, very good on the ball, would never lose it, and could definitely be a decent player.
‘He trained with the first-team a couple of times. Ben was probably one of the ones they wanted to get over and test because he was one of the better ones.
‘I also recognise Brandon Haunstrup. I would have seen him around and can remember the name, but never saw him play. They’ve all grown-up now.’
Bird quit plumbing to become a Pompey player in July 2013 – however has since returned to the trade.
After leaving the Football League in the summer of 2017, the 30-year-old picked up the tools once more.
He added: ‘I’ve gone back to being an electrician.
‘Maidenhead are part-time, so I work in the day and train Tuesday and Thursday evenings.
‘I didn’t have to go go back to it, but I didn’t want to sit down in the day and be bored. There are so many series to watch on the television.
‘I can get a bit bored so thought I’d get the tools out and get back in the game. I have a mortgage to pay you know!’