Caleb was born in Leeds and progressed through the youth set up at Leeds United before gaining a professional contract with the club. After failing to make the first team, he joined Diamonds on a one month loan on 4 October 2001, making his Nene Park debut the following day as a second half substitute against Hartlepool United. Although the striker only made two starts, he was popular with the crowds for his explosive pace for such a tall player although he failed to score during his time with Diamonds.

After his return to Leeds, he spent a month on loan at Hull City later in the month. He was released by Leeds in February 2003, joining Chesterfield on a free transfer. Despite a knee operation in April 2006, he had four successful years with the Spireites, and earned a £500,000 move to Wigan Athletic in January 2007 during their inaugural Premiersip season. He scored twice in sixteen appearances. On transfer deadline day (31 August 2007), Championshp side Hull City paid £1million to acquire the striker as he helped the Tigers attain Premiership status, although he was stretchered off in his debut game at Blackpool although the injury proved not too serious. With his grandparents coming from the Republic of Ireland, he joined the international squad for the European Championship qualifier against Cyprus In October 2008, coming on as a late substitution. On 17 September 2009, he went out on a three month loan to Championship side Middlesborough, before returning to Hull City. After not being part of Hull's future plans, he was released from his contract and signed for Major League Soccer club Colorado Rapids on 16 March 2011.

Appearances

2001/2002 - squad number 31

D3	5.10.01	Hartlepool Utd(H)	as sub
D3	13.10.01	Rochdale (A)
LDV1	16.10.01	Cardiff City (A)
D3	20.10.01	Hull City (H)	as sub
D3	23.10.01	Shrewsbury Tn (A)	as sub
D3	27.10.01	Mansfield Town(H)	as sub
D3	3.11.01	Swansea City (A)	as sub