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.
He participated 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.