Career
Thackray started his career with Newcastle United, but was released at the age of 16. He signed for the then Italian Serie A side Reggina, after being spotted playing in tournament for England Colleges XI. He spent his first professional season on loan with Lega Pro Seconda Divisione club Monopoli, where he was awarded Monopoli's Player of the Season. He played on loan to Reggina"s fellow Serie B side, Ancona He played ten games at Ancona.
On July 2010 he was sold to Lega Pro Prima Divisione club Fidelis Andria in a co-ownership bid.
Later on January 2011 he was loaned to Cosenza, another club from Lega Pro Prima Divisione. He scored his first professional goal for Cosenza against Pisa on the 13th of February.
In July 2011 he ended his contract with Reggina Calcio for the chance to return home to England. After trialing with Huddersfield Town Football Club, Wrexham Football Club and Gateshead Football Club Thackray received an offer from Maltese Premier League side Qormi and signed in January 2012.