After playing for various amateur sides, he joined Norwich City in 1919, moving on to Middlesbrough the following year.

In the 1930s, he enjoyed short spells at Stockport County and Burnley before settling in France with Olympique de Marseille and Club Français.

He quickly returned to the Third Division South with Brighton & Hove Albion, who posted a fifth-place finish in 1925–26.

He spent 1928–29 with Nottingham Forest, and was the club's top scorer in 1928–29 with 17 goals in league and cup competitions.

[2] He hit two goals on the opening day of the 1931–32 season, in a 3–1 win over Plymouth Argyle at Home Park.

Jennings moved on to Club Français of Ligue 2 before returning to England to play for Scarborough and Wisbech Town.

He died at Darvel Hall in Robertsbridge on 21 August 1944 – he had two bouts of pneumonia which made him prone to chills – and was buried at Hastings crematorium eight days later.