Simon arrived at the Deeside Stadium ahead of the 2013-14 season following two spells at Nantwich Town. Simon enjoyed a brief spell at Stafford Rangers between his two stints at Nantwich, and has also spent time at Crewe FC, where he scored 12 goals in three games and Kidsgrove Athletic.

As a 17 year old, Simon was offered a 12-month YTS contract with Hull City. A Crewe lad born and bred, he reluctantly passed up the opportunity with Hull due to commitments to his hometown side.

Simon joined Penycae FC in the Huws Gray Cymru Alliance in January 2014 on loan, and left The Nomads for Conwy Borough ahead of the 2014-15 season.