Following the critical and commercial success of I've Been Expecting You (1998), the North American release of The Ego Has Landed (1999) and the subsequent promotional tours for both albums, Williams reteamed with producers Guy Chambers and Steve Power to create new material for his next record.

Whereas I've Been Expecting You used the Britpop genre for its overall sound, Sing When You're Winning incorporates a more post-millennial dance-pop approach while utilizing classic British rock elements.

Sing When You're Winning debuted at number one in the UK, Germany, Ireland and New Zealand, as well as the top 10 in countries like Australia, Finland, Sweden and Switzerland.

[3] The sound of the album was described as seeing Williams move "farther away from the increasingly dated visions of Oasis-style Britpop to embrace post-millennial dance-pop, complete with the bruising beats and extroverted productions to match.

The images were taken by photographer Paul M. Smith and, along with Williams' complete football strip, were later sold at auction to raise money for his charity Give It Sum.