Jennings began his career with his hometown club Stockport County and joined Wigan Athletic in 2012. He went on loan at Accrington Stanley in March 2015 but failed to make an appearance for Stanley through injury.[1] He made his professional debut on 11 August 2015 in a 2–1 League Cup defeat against Bury.[2] On 12 November 2015, Jennings joined National League side Cheltenham Town on an initial one-month loan deal.[3]
In September 2016 Jennings joined National League North side AFC Fylde,[7] but by December he had joined local league rivals Curzon Ashton. On 15 June 2017 he penned a one-year deal with Alfreton Town. During his time at Alfreton he received a call up for England C as back up but never made an appearance .[8]