Chaplow memulai karier juniornya di klub [[Burnley F.C.|Burnley]], kemudian memulai karier seniornya di klub tersebut.<ref name="ClaretsMad">{{cite news|date=2 February 2005|url=http://www.clarets-mad.co.uk/news/loadfeat.asp?cid=ED94&id=203006
|title=Richard Chaplow feature|publisher=ClaretsMad!|accessdate=22 August 2007}}</ref> Pindah ke [[West Bromwich Albion F.C.|West Bromwich Albion]]<ref>{{cite news
|date=31 January 2005|url=http://news.bbc.co.uk/sport1/hi/football/teams/w/west_bromwich_albion/4223251.stm|title=West Brom complete Chaplow deal|publisher=BBC Sport|accessdate=27 May 2007}}</ref> yang sempat meminjamkannya ke [[Southampton F.C.|Southampton]],<ref>{{cite news|date= 8 February 2006|url=http://news.bbc.co.uk/sport1/hi/football/teams/w/west_bromwich_albion/4686100.stm|title=Chaplow completes Saints switch|publisher=BBC Sport|accessdate=27 May 2007}}</ref> Chaplow kemudian pindah ke [[Preston North End F.C.|Preston North End]]<ref>{{cite news|date= 9 January 2008|url=http://news.bbc.co.uk/sport1/hi/football/teams/p/preston/7179992.stm|title=Preston complete deal for Chaplow|publisher=BBC Sport|accessdate=9 January 2008}}</ref> yang juga sempat meminjamkannya kembali ke Southampton.<ref>{{cite web|date= 30 September 2010 |url=http://www.saintsfc.co.uk/page/NewsDetail/0,,10280~2170637,00.html|title=Chaplow Joins On Loan |publisher=Southampton FC|accessdate=1 October 2010}}</ref> Hingga kemudian bergabung dangan Southampton pada tahun 2011.<ref>{{cite web|url = http://www.saintsfc.co.uk/page/NewsDetail/0,,10280~2254344,00.html|title = Chaplow Agrees Move|date =30 December 2010|publisher=saintsfc.co.uk|accessdate =30 December 2010}}</ref>
