He played in both legs of the 2004 FA Youth Cup Final, which Middlesbrough won 4–0 on aggregate. Knight signed a professional contract with Middlesbrough on 3 February 2005 and his first involvement with the first team came weeks later after being named on the substitutes' bench for a 2–2 draw with Charlton Athletic in the FA Premier League on 27 February. Knight joined League Two team Darlington on an emergency one-month loan on 30 December 2005 to cover injuries to Sam Russell and Bertrand Bossu and he made his debut the following day in a 2–2 draw against Lincoln City.
The player participated in both legs of the 2004 FA Youth Cup Final, which Middlesbrough won with a 4-0 aggregate score. He signed a professional contract with Middlesbrough on February 3, 2005, and his first appearance for the first team came weeks later after being named as a substitute in a 2-2 draw against Charlton Athletic in the Premier League on February 27th. Knight joined League Two team Darlington on loan to cover injuries to Sam Russell and Bertrand Bossu, making his debut the following day in a 2-2 draw against Lincoln City.