He was just 20 when he helped the south-coast outfit to the semi-finals of the FA Cup, where they lost on penalties to Liverpool. His move to Spurs followed later that summer.
But despite 29 England caps and appearances in a World Cup and European Championship to his name, Darren can only use one word to sum up his 10 years at Spurs.
“Frustrating,” he said. “It’s been frustrating because of the injuries. The first four, five years were brilliant and then it’s been frustrating.
“As a team we’ve only won the Worthington Cup, so that’s been frustrating and then, personally, because of the injuries. When I’ve played I’ve been okay, I think, but it’s just been about the injuries.”
Darren, now 29, says he doesn’t want to be remembered for those injuries — and that dreaded ‘Sicknote’ nickname.
“I don’t want to be remembered for the injuries, of course not,” he declared.
“That’s just the way it’s going to be until I can get a few seasons under my belt where I’m not picking injuries up.
“The problem has been it hasn’t been little injuries, they’ve all been serious ones.
“If I get a tweak now perhaps that’s when I’ll take easier in training rather than carrying on because I want to play all the time. Maybe I’ll take more rest and then the little niggles go away and don’t turn into something more serious.”
So was he looking forward to hearing the Pompey chimes again?
“That’s where it all began for me so it’s always nice to go back down there,” he added. “Ten years? That seems a long time.
“I remember growing up at Portsmouth, just getting to know the game from the youth team to the first team with lots of my friends in what was quite a good youth team there.
“We all broke into the first team at about the same time and then we had that great season and FA Cup run. I’m looking forward to going back.
“Pre-season is going well. It’s hard coming back from an Achilles injury because of the hard ground at this time of year, so I have to be careful. But I’m very happy so far.”
By Paul Miles
Darren Anderton returns to Portsmouth tonight almost 10 years after the season that made him the hottest property in English football.