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.
. Most expensive signings
Every League One clubs most expensive signings. Photo: Christopher Lee
. Cheltenham - Jermaine McGlashan
Estimated fee: £50,000; Moved from: Aldershot; Year: 2012. Photo: Pete Norton
. Exeter - Jayden Stockley
Estimated fee: £100,000; Moved from: Aberdeen; Year: 2017. Photo: Pete Norton
. Stevenage - Scott Laird
Estimated fee: £100,000; Moved from: Plymouth; Year: 2007. Photo: Pete Norton
. Northampton - Josh Low
Estimated fee: £165,000; Moved from: Oldham; Year: 2003. Photo: Pete Norton
. Cambridge - Steve Claridge
Estimated fee: £252,000; Moved from: Luton; Year: 1992. Photo: Julian Herbert
. Wycombe - Darren Currie
Estimated fee: £270,000; Moved from: Barnet; Year: 2001. Photo: Pete Norton
. Leyton Orient - Justin Channing
Estimated fee: £286,000; Moved from: Bristol Rovers; Year: 1996. Photo: Alex Burstow
. Lincoln - Dany N'Guessan
Estimated fee: £338,000; Moved from: Rangers; Year: 2006. Photo: Michael Regan
1. Most expensive signings
Every League One clubs most expensive signings. Photo: Christopher Lee
2. Cheltenham - Jermaine McGlashan
Estimated fee: £50,000; Moved from: Aldershot; Year: 2012. Photo: Pete Norton
3. Exeter - Jayden Stockley
Estimated fee: £100,000; Moved from: Aberdeen; Year: 2017. Photo: Pete Norton
4. Stevenage - Scott Laird
Estimated fee: £100,000; Moved from: Plymouth; Year: 2007. Photo: Pete Norton