Jennings started his career with Cadzow St Anne's and had a trial with Tottenham Hotspur in 1919, playing no games for the club.
[1] He made 167 league appearances for the club, in which he scored 112 goals, before he joined Chester in June 1931.
[1] Jennings officially scored Chester's first ever Football League goal in a 1–1 draw with Wrexham on 2 September 1931.
His tally of five goals in one game has only been matched once (by Barry Jepson in 1958) and never bettered by a Chester player in a Football League fixture.
[3] Jennings also scored four times in a 7–2 win over Rochdale in April 1932 and comfortably ended the season as Chester's top scorer, with 30 league goals to his name.