It was a two-year south-coast stay that ended and began in protracted transfer sagas.
But for former Pompey skipper Darren Moore, his eventful spell at the Blues is best remembered by the ‘fabulous’ relationships he shared with teammates, fans and the city itself.
A no-nonsense centre-half and natural leader of men, it is perhaps unsurprising that Moore donned the armband or that the Fratton faithful took him to their hearts in a period of disarray on and off the field of play.
Indeed, an early examination of Moore’s character arrived when the man who had attracted him to the club in the first place, Alan Ball, was sacked just one month after the defender had made the November 1999 move to PO4.
The switch in itself was far from plain sailing, with a summer fall-out at newly-promoted Premier League side Bradford City sparking an exhaustive bidding war between a number of clubs for the Jamaica international.
A call out of the blue from Ball, though, ensured Moore’s services were snatched from a collection of other suitors for a fee of £500,000.
He said: ‘There was a lot of confusion in it (the transfer).
‘I was at Bradford City, who had just got promoted to the Premier League but in between, Glasgow Rangers had come in for me.
‘At one point, there was Rangers, Nottingham Forest, Sheffield United, Barnsley and Portsmouth all after me and a lot of toing and froing between the clubs.
‘When I actually moved to Portsmouth it had taken about eight weeks for it all to happen because all these other clubs were still interested.
‘A lot of things needed sorting out – the Portsmouth offer itself had actually gone cold for about six weeks.
‘But then out of the blue, the wonderful man himself, Alan Ball got hold of me and what he said made a lot of sense really.
‘I decided that I just wanted to play football again.
‘So he said to me to come down to Portsmouth, be a part of something and help get this great club going again.
‘Once it was clear and evident for me to make the move, I didn’t have a moment’s hesitation.’
The banter Moore received from his old Bantams team-mates heightened, though, when new boss Ball was relieved of his duties less than a month later, with the Blues struggling at the wrong end of the division one table.
Moore said: ‘It’s funny in a way because when I left Bradford all the players there rang me up and made a joke saying Alan Ball had only seen me play in one training session and had left the club!
‘I think it’s fair to say the club was in a little bit of disarray at the time after him leaving.
‘At that point, obviously I had only been down there for a month.
‘But I had signed for a wonderful club and there were some good people around, so I still felt at home despite what was happening.’
A period of transition saw Tony Pulis emerge as the Blues’ new boss in January 2000.
His remit was to lead the club he inherited in a relegation position to safety – a task he duly achieved by a five-point margin.
The fans’ frustrations at their team’s underachievements were best demonstrated by the month of March, where Pompey effectively secured their division one status with five wins from their seven matches.
Moore said: ‘We were fighting relegation and in and around the bottom of the league but we had a talented team there – we just couldn’t seem to get it going.
‘On our day, as we showed, despite being down at the bottom, we were a match for anybody.’
Despite a largely disappointing Blues campaign, Moore – nicknamed ‘Bruno’ after his similarity in appearance to the boxer Frank – had grown in popularity with both the Fratton faithful and management.
And his committed displays at the heart of defence saw him awarded the captain’s armband by Pulis at the beginning of the 2000-01 season.
Moore said: ‘Tony made me team captain, which was a huge honour for me.
‘It was great to be skipper and also for the Fratton faithful to take to me and my no-nonsense approach to football – which was a big part of my game.
‘It was a good match for myself down there.
‘I settled in well and moved into a new house in Warsash – everything was really, really good.’
On the field, though, the same old struggles emerged, with the Blues’ seemingly annual battle with relegation going to the wire.
A final-day 3-0 victory at home to Huddersfield saw the Terriers relegated in their place as the Blues survived by a solitary point.
Moore’s equalising goal at Gillingham earlier in the season – only his second for the club – took on added significance, although the stalwart’s failure to remember scoring for Pompey is easily forgiven.
He said: ‘I don’t remember either of them!
‘My thing was just trying to keep the ball out at the other end.
‘My game was about keeping my team-mates organised and disciplined.
‘I was trying to be hard to beat, and considering everything that was going on, all my focus was on keeping Portsmouth’s division one status – which we did.’
The chaos alluded to by Moore centred around the Blues employing three different managers that season, with Pulis succeeded by player-manager Steve Claridge and former Chelsea assistant Graham Rix.
Rix’s arrival proved bitter-sweet for Moore, though, after seeing his promising defensive partnership with Linvoy Primus torn apart by a bombshell training-ground revelation at the start of the 2001-02 campaign.
He said: ‘Myself and Linvoy formed a formidable partnership.
‘We were settled under Graham but it was only a short time into Graham’s spell in charge that I got told by his assistant Jim Duffy I was not going to travel to Stockport (in August 2001) because they had accepted an offer from a football club (West Bromwich Albion).
‘A lot of people, myself included were really surprised.
‘But when a club comes to you and says they have given you permission to speak to another club, it is their way of saying “you can go”.
‘I remember Graham saying to me at the time that the club had good money on the table for me (£750,000) and it was money that they needed.
‘Because me and Linvoy were both there, the club decided they only needed one of us – and there was money on the table for me.’
For Moore, it marked the end of a whirlwind two-year stay at the Blues which took in 64 games, four managers, two goals and as many relegation dogfights.
But in keeping with his Fratton Park arrival, Moore’s exit from the club was not straightforward.
He said: ‘The transfer didn’t go through for another few weeks, so I just didn’t play.
‘I was just sat there kicking my heels – it was something to do with the amount of money agreed between the two clubs.
‘It was getting to be really frustrating because this was a club interested in me from the Midlands, where I was from.
‘In the end, though, it went through.
‘But I left the club with only fond memories of the fans, all of my team-mates and the city of Portsmouth, which had been a home to me for two years.
‘I had a fabulous time down there and I always enjoy coming back to visit the city.’
Moore, aged 40, went on to play in the Premier League with the Baggies and is now working for them as their professional development phase coach.
DARREN MOORE ON...
...FOND FRATTON MEMORIES
I always look back on both Portsmouth itself and Fratton Park with fond memories.
The many thousands of fans the club used to take to away matches all over the country and the way they would get behind us for the full 90 minutes was really something.
It was playing at home, though, that was extra special.
I also loved it down there because in and around the city of Portsmouth all of the kids wore their Pompey shirts with great pride.
And whenever I come back down to Portsmouth to see my good friend Linvoy (Primus), I always make sure I make a trip down to Southsea just to see the city itself and how it has changed.
The boys I played with at Pompey had talent, there’s no question of that.
We shouldn’t have been fighting relegation battles with the likes of Lee Bradbury, Steve Claridge, Nigel Quashie and Ceri Hughes in the side.
Awfs (Andy Awford) was just retiring when I arrived but was a good player also.
The Rooney Rule (In American Football, NFL clubs must interview at least one black or ethnic minority candidate for each head coach or senior football operation vacancy) is a way of asking for a fair chance in the interviewing process when jobs become available –that’s it.
The reason why we are asking the question is because of the statistics within the game.