Ben Chamberlain began his footballing career at Everton as a nine year old. The following year he joined Chester and at the age of 12, he signed for Manchester City. Two years later, he joined Blackburn where he would later sign a professional contract and play for their Under 17s and Reserve sides. During this time, he won Welsh Under-15 schoolboy honours.

Aged 18, Ben played for the Canaries in their 4-1 Reserve team victory over Barnet in February 2001. In the summer of 2001, Ben had trials with Stoke, Chesterfield and Carlisle (vs Northwich on July 28th 2001) before joining Welsh side Newtown following advertising his services on footballcv.com

Ben later joined Buckley Town of the Huws Gray - Flitlock Cymru Alliance before moving to Holywell Town in October 2004.