The £11m signing from Liverpool proved his worth in his second spell at the club, netting 11 goals in 38 outings in the Premier League.
He would go on to join Spurs in July 2009 - reuniting with former Blues boss Harry Redknapp at White Hart Lane.
But how does the Blues’ record purchase compare?
We’ve taken a look at the most expensive signings made by each League One club to see where Crouch and Pompey’s figure ranks.
Here’s what we found.

9. Lincoln - Dany N'Guessan
Estimated fee: £338,000; Moved from: Rangers; Year: 2006. Photo: Michael Regan

10. Bristol Rovers - Andy Tillson
Estimated fee: £370,000; Moved from: QPR; Year: 1992. Photo: Chris Lobina

11. Shrewsbury - Lionel Ainsworth
Estimated fee: £370,000; Moved from: Huddersfield; Year: 2011. Photo: Pete Norton

12. Fleetwood - Kyle Dempsey
Estimated fee: £410,000; Moved from: Huddersfield; Year: 2017. Photo: Pete Norton