Duckworth spent the early part of his career as an attacking player at York City and Harrogate Railway before starring at right back for Bradford Park Avenue in the Conference North in 2012/13. His performances earned him player of the year awards from supporters and players alike. Pools manager Colin Cooper handed the 21-year-old a trial in the summer of 2013 and gave him a first start in a Pools shirt in a friendly at Whitby Town. The trial proved to be a fruitful one for Duckworth. After impressing in a couple of friendlies and reserve games, he was handed a short-term contract in August 2013 and quickly established himself as a fans' favourite. His performances in his first few months of league football also made an impression on the management, and he was offered an improved deal before the year was out.