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Born in Zambia, Whitley moved to England at the age of seven. He first played for the England under-17 team, and in 1996 joined Manchester City as a midfielder. As his father was born in Belfast he was eligible to play for three international teams: Northern Ireland, Zambia, or England. He chose Northern Ireland and played his first game for them in a friendly match against Italy in 1997. He was also the first black player to play for Northern Ireland.
In 2003 he moved to Sunderland to join his international teammate George McCartney at the Stadium of Light.

Notable goals include one against Wales in a 2004 World Cup qualifier in Cardiff, and against West Ham United in 2004, when he actually scored with a tackle.

At the end of the 2004/2005 season, after helping them to win the Football League Championship, Sunderland released Whitley from his contract. And later he signed for Cardiff City.
He also has a brother Jim who formely played professionally, but was forced to retire due to injury. Jeff was sent home from the Northern Ireland squad for disciplinary reasons as he missed a curfew set by manager Lawrie Sanchez.

Whitley was on loan to Stoke City from late 2006 until January 2007. However, he struggled to make an impact and ony made one start for the club in an under strength Carling Cup team, in a 2-1 defeat to Darlington.

Whitley recently went AWOL from Cardiff City with the Club, and his agent, unable to contact him. This prevented the club from being able to transfer him during the January Transfer Window.
On 16 February 2007 it was announced that Whitley would be joining Wrexham FC on loan for the remainder of the season. Whitley would score the vital winning goal on March 24, 2007 away against Bristol Roversin a 1-0 victory.
He was released by Cardiff upon his return to the club.