Career
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. He made his professional debut on 11 August 2015 in a 2–1 League Cup defeat against Bury.
On 12 November 2015, Jennings joined National League side Cheltenham Town on an initial one-month loan deal.
On 15 February 2016, Jennings joined National League side Grimsby Town on loan until the end of the season.