It was an inauspicious start as Svetoslav Todorov was sent off in a 2-0 defeat at Preston in 2002, with little sign of the success which was to follow.
Now, two decades on, can you remember the players who made up that Blues squad at Deepdale? There may well be one or two who’ve slipped your mind…
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5. Nigel Quashie
Played for Pompey in the Premier League before crossing the divide for Southampton in 2005. Now runs Improving Players Development Academy. Photo: Craig Prentis
6. Garry Brady
Returned north of the border after leaving Pompey in 2002, playing for likes of Dundee and St Mirren. Involved in charity work helping childen in deprived areas play football. Photo: Jamie McDonald
7. Mark Summerbell
Had five games on loan at Pompey and later played for Carlisle , number of non-league sides and then Sunday league football for Durham and District side Framwellgate Moor Salutation. Photo: Ben Radford
8. Gary O'Neil
One of the youngest players to play for Pompey. Went on to have a fine career for likes of Middlesbrough, West Ham and QPR. Now a coach at Bournemouth. Photo: Phil Cole