With both teams vying for a place in the Round-of-32 of the UEFA Cup, one of the most memorable Fratton Park nights in the club’s history unfolded.
But it was to be late heartbreak for the Fratton faithful as goals from superstars Ronaldinho and Filippo Inzaghi late-on secured progress for the visitors.
However, the fixture will live long in the memories of those who were there including the former Barcelona forward who described the PO4 atmosphere as ‘the best in the world’
After the latest anniversary of the clash, we’ve looked into what those who wore royal blue against the the Rossoneri are up to now?
Click through the list to see what happened to the Pompey players from that evening.
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1. GK: David James
David James was a much-loved figure in PO4 and spent four memorable years at the club. James moved onto Bristol City in 2010 before spells at AFC Bournemouth, IBV Vestmannaeyjar in Iceland and Kerala Blasters in India before retiring in 2014. James then had a brief spell as manager of the latter before being dismissed and now appears on BT Sport and Talksport as a pundit. Picture: John Walton
Photo: John Walton
2. RB: Glen Johnson
Johnson joined the club after a successful loan spell from Chelsea in 2006-07 and was an ever-present for the club before moving to Liverpool in 2009. The right-back lifted the FA Cup in 2008 and finished his career at Stoke City following their relegation to the Championship in 2018. He is now focused on his ventures after establishing a property development business with his brother, and can also be found as a pundit for beIN sports, TalkSPORT and Sky Sports. Picture: PA Wire/Press Association Images
Photo: Anthony Devlin
3. CB: Younes Kaboul
Kaboul scored Pompey's opening goal against Carlo Ancelotti's side but his spell on the south coast was brief after following Harry Redknapp back to Spurs in 2010. The centre-back enjoyed five years at White Hart Lane before spells with Sunderland and Watford. After walking away from the game, Kaboul has opened his own care home for those with mental disabilities in Belgium. Picture: PA Wire/Press Association Images
Photo: Anna Gowthorpe
4. CB: Sylvain Distin
Distin grew in prominence during his stay on the south coast and became one of the Premier League's best defenders. He eventually left for Everton in 2009 where he continued his strong form in defence. Distin then moved to AFC Bournemouth, where he now works as a strength and conditioning coach privately in Dorset. Picture: Daniel Hambury
Photo: Daniel Hambury