Career
Cowler played for Frinton & Walton YFC before signing a youth scholarship with West Ham United in 2009. He then spent time on loan with the youth teams of Wycombe Wanderers, Queens Park Rangers, Yeovil Town and before being released in May 2012, his only appearance in a first team squad coming when he was on the bench for a Football League Cup game against Aldershot Town on 24 August 2011. Having previously spent time on loan in their youth team, in June 2012 he signed foreign
Cowler made his debut for on 29 September 2012 in a 2–1 away defeat to Fleetwood Town, coming on as a 24th minute replacement for Ahmed Abdulla as a result of first choice goalkeeper Graham Stack being sent official
In July 2013, Cowler announced his departure from on Twitter, as he wanted first-team football and was unable to displace the reliable Graham Stack as first choice. The following month, he signed for Bishop"s Stortford on a one-year deal.
Cowler re-joined on a one-year deal on 4 August 2014, once again as backup to Stack. At the end of the season he left the Bees, again to seek first-team football.
Cowler then signed for Isthmian League side Heybridge Swifts in August 2015, before joining Brightlingsea Regent in January 2016.