Before joining Boston United in August 2004, Staff played non-League football for clubs including Rushden & Diamonds, Stamford and King's Lynn,[2] who he joined on transfer deadline day in 2002, making his Linnets debut on 1 April 2002 against Cambridge City.

[3] Despite King's Lynn's relegation to the Southern League Eastern Division at the end of that season, Staff remained with The Linnets.

He scored 20 goals in all competitions in the 2002/03 season, and was King's Lynn's leading scorer in the 2003/04 season with 23 goals in all competitions, helping King's Lynn to the Southern League Eastern Division title and promotion back to the Premier Division.

In February 2004 he scored directly from a corner kick in King's Lynn's 4–1 victory over Banbury United.

He left King's Lynn for Boston United in the summer of 2004, making his Football League debut on 21 August 2004 as a very late substitute in the League Two game against Macclesfield Town which finished 1–1,[4] but failed to establish himself in Boston's first team and returned to King's Lynn.