More than 14 years ago they were Wolves strike partners inspiring a 6-1 hammering of Bristol City.
Today they occupy the same changing room, only Guy Whittingham is the boss these days.
In David Connolly, though, Pompey’s caretaker manager sees a former team-mate whose ability, commitment and conduct left an indelible mark on his memory.
That was the driving force behind Whittingham bringing the 35-year-old out of the footballing wilderness and into Fratton Park at the turn of the year.
Connolly has made an impressive impact during his brief time with Pompey, netting his maiden goal in a man-of-the-match display against MK Dons on Tuesday.
It certainly had Whittingham purring afterwards, having played alongside the much-travelled striker during a two-month loan spell from Sheffield Wednesday in the 1998-99 campaign.
With Molineux the setting, they netted six goals in six matches as a strikeforce – albeit five of them coming in the same match against Bristol City.
That November 1998 occasion at Ashton Gate saw Connolly grabbing four, Whittingham another and future Pompey midfield Carl Robinson completing the 6-1 rout.
Whittingham would return to Wednesday the following month after 10 appearances for Wolves, while Connolly, who was on loan from Feyenoord at the time, left at the end of the season.
Now they are reunited again, this time on the south coast.
Whittingham said: ‘David is fantastic and a player I have know for a long, long time. When I went to Wolves on loan he was there as a player and always looked after himself and did the right things.
‘He does everything right, is a model pro and not only a good player but a good role model for the younger lads here.
‘David has just got a great attitude to playing football. There are the odd ones about, you look at Kevin Phillips and Ryan Giggs, there are players at all levels who do that.
‘I put him in the team on Tuesday night because he gives that little bit of experience.
‘He wants to win, he is desperate to win, and he’s not afraid to let people know out there he wants to win.
‘He and Liam (Walker) had a set-to out on the football pitch and you want to see that because it shows the desire.
‘He’s a great influence and the work-rate he puts in is phenomenal.’
Since effectively replacing Izale McLeod in the Pompey squad, Connolly has made seven Blues appearances.
Yet when he arrived in January he had been without a club since being released by Southampton at the end of last season.
Now the veteran has opened his account – and Whittingham is hoping for more.
He added: ‘I hope David will get more goals. Certainly if he keeps putting in performances like that we will keep picking him.
‘Each match we will look at teams we are playing against and use the players we have got the best way we can. There is competition for places, especially up front.
‘We have five players up there, possibly. People forget Ashley Harris, but he’s a striker as well who I thought did well when he came on in the second half against MK Dons to try to give that bit more energy.’