He was a pupil at Turton Media Arts College in Bromley Cross, Bolton before turning professional and moving to America to pursue a career in football.

After posting remarkable scoring totals at NCAA Division II Fort Lewis College in Durango, Colorado, and in the USL Premier Development League, for Boulder Rapids Reserve, Cunliffe was one of the leading prospects at the MLS combine prior to the 2007 MLS SuperDraft.

Cunliffe also had a brief spell at English Northern Premier League First Division North outfit Rossendale United in 2005–06.

He made his MLS debut on 7 April against Toronto FC and assisted on the clinching goal in a 2–0 win.

He scored his first goal with the Earthquakes on 31 May 2008 in a 3–1 to loss to Real Salt Lake, a rocket shot from within the penalty area.