He signed his first professional contract in May 2009, then in July he played for the first team in the pre-season South West Challenge Cup held in North Devon, including playing in the 5–0 win over Barnstaple Town.
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On 29 August 2012, Eastham joined Blackpool's Fylde coast neighbours Fleetwood Town on a one month loan deal, together with team-mate Tom Barkhuizen who joined on loan for six months.
Ashley Olsen | Ashley Judd | Ashley Tisdale | Laura Ashley | Ashley Giles | Robert Ashley | Moses Ashley Curtis | Ashley | Ashley Walters | Ashley Slater | Ashley Martin | Ashley Harkleroad | April Ashley | William Henry Ashley | Mary-Kate and Ashley Olsen | George Eastham | Elizabeth Ashley | Ashley Planes | Ashley Monroe | Ashley MacIsaac | Ashley Cole | Ashley Abbott | Ashley Mallett | Ashley Hutchings | Ashley Cooper | Ashley Brehaut | Ashley Beedle | Anthony Ashley-Cooper, 7th Earl of Shaftesbury | George and Ashley Abraham | Ashley Wood |
On 29 August 2012 Barkhuizen joined Blackpool's Fylde coast neighbours Fleetwood Town on loan until January 2013, together with team-mate Ashley Eastham who joined on loan for one month.