Strathaven, Lanarkshire born centre forward Tommy Jennings started his career with Strathaven Academy in 1917, playing junior football for Earnock Rovers and Glasgow Ashfield in 1918 before winning a Scottish Juvenile Cup-Winners’ medal with Cadzow St Anne’s in 1919. He had an unsuccessful trial with Tottenham Hotspur in 1919, then joined Raith Rovers in January 1921, for whom he became a regular goalscorer, playing alongside the likes of Alex James and Jimmy McLelland in their free scoring attack, scoring 73 goals in 134 games for Raith over the next 4 seasons.
He joined First Division Leeds United in March 1925, making his Football League debut against Sheffield United the same month. In his first full season of 1925-26 he was an ever-present and topped the list of scorers with twenty-six goals to make him Leeds’ highest scorer in one season, breaking Jack Swan’s previous club record. He missed only one game in the following season but with the advent of the new offside laws he scored thirty-five goals, including three successive hat-tricks, a feat equaled only by Gilbert Allsopp in 1939 and Liverpool’s Jack Balmer in 1947. However, despite Jennings’ deadly marksmanship, United were relegated that season.
Described as “a fine, forceful player, a grand leader and a dead shot, he has proved to be a prolific goalscorer, he then scored 21 goals as Leeds bounced straight back with promotion as Second Division runners up in 1927-28. His subsequent career with Leeds was punctuated by absences from the first team due to blood poisoning. He made 174 appearances for the club, in which he scored 117 goals, before he joined Chester in June 1931 and remains Leeds’ 4th highest goalscorer of all time.
At Sealand Road Jennings officially scored Chester’s first ever Football League goal in a 1-1 draw with Wrexham on 2nd September 1931. Although Chester had beaten Wigan Borough 4-0 four days earlier (with Jennings scoring the third goal), the result was deleted after Wigan resigned from the Football League in October 1931.
Later in the season he scored Chester’s first Football League hat-trick, when he scored all the club’s goals in a 5–1 win over Walsall in January 1932. 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. 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. But he only played nine more league games for the club after this and moved on to play for and manage Bangor City in 1933 after 34 goals in 50 appearances.
Jennings later managed Third Lanark from 1934 to 1939.