 He played 20 games across the 2016–17 campaign after overcoming a knee injury which required surgery.Jennings signed with National League North club Southport in June 2017, and was described as a "massive coup" for the "Sandgrounders" by manager Alan Lewer.On 3 November 2017, he joined Northern Premier League Premier Division side Warrington Town on a two-month loan deal; "Yellows" manager Paul Carden said that "Jenno is a player I know well and the opportunity to sign him was too good to turn down".