Jim is the oldest of the Whitley brothers, and also a product of Citys youth policy. He had a difficult start of his career, and was once more reputed for his off-pitch activities than of his fine playing capabilities. City stood by their young offspring, and he came back like a bullet in the 1997-98 season and was voted young player of the year. It was in Citys darkest moments in division 2 that Jim got the chance to show his full potential and he did well alongside Pollock and Horlock, to help City gain promotion.
Back in division 1 life was again getting difficult, this time on the pitch. Even his brother Jeff couldn't help the situation, and playing two Whitleys in midfield at the same time never seemed likely. Jim then went on loan to Blackpool, to seek regular 1st team play, a move that cast him right back into the 2nd division struggle, but it proved successful for his younger brother the previous season to spend some time away from Maine Road.
On 24th August 2000, Norwich signed Jim on a month's loan. The 25 year old (at the time) Northern Ireland international midfielder was known to the likes of Bryan Hamilton and Nigel Worthington. Jim had made 38 appearances for Man City but was on their transfer list. He has also spent a loan period at Blackpool where he made 8 appearances.
Although Jim's loan was extended until the end of October 2000, he returned to Man City on 26th October, replaced by Danny Granville heading to Carrow Road on loan the following day.
Jim later headed to Swindon on loan but played just 2 games. On returning to Manchester, it was suggested that he would rejoin Blackpool at the end of the 2000/01 season as he would be available on a Bosman Free Transfer. The BBC Ceefax service reported on 27th February 2001 that Jim had joined Northampton on loan for whom he made 13 appearances
Jim signed for Wrexham on August 1st 2001.