Represented Wood Green, Middlesex and England Schoolboys and was picked to be a ball-boy at the 1932 FA Cup final between Newcastle United and Arsenal at Wembley.

First joined Spurs as an amateur in 1935.

He progressed through the club's Junior side and their played for the Northfleet nursery side before becoming the club's regular inside-right during the run up to World War II.

Went on to make over 300 first team matches for the side and then finished with a spell at West Ham.

Signed professional in May 1939 and hit a hat-trick on his first team debut in November 1939 against Watford.

In World War II he was a guest player for Torquay United and Distillery and represented the Northern Ireland Regional League against the League of Ireland in April 1943.

Served in the Army in Burma, India and Egypt.

After the war he returned to the Tottenham first team.

Made his Football League debut, aged 28, against Birmingham on 31st August 1946 and scored his first League goal in his next game against West Bromwich Albion.

In 1946 Les represented the FA XI against The Army and The Navy and later against Cambridge University and Diable Rouge (a Belgian Select XI).

Was top scorer in the 1946-47 season with 16 League and one Cup goal and was top scorer again in 1948-49, when he was ever-present and scored 19 League goals.

Won a Second Division Championship medal in 1949-50 and a First Division Championship the following season in the "push and run" Spurs team under Arthur Rowe.

Had a great striking partnership with Len Duquemin and he is the seventh highest League goal-scorer in Spurs history. But he was nto just a goal-scorer, because he was thought of as an entertaining ball player whose positional sense created many openings for both himself and for others.

In 1951-52, Bennett top scored with 20 League goals, his best total, as Spurs finished in runners-up place in the First Division Championship.  He almost won an England cap, as in 1951-52 he stood by as an England reserve but neevr got the call up to the national side.

In December 1954 he moved to Second Division West Ham United and scored three goals in 26 League and one in two FA Cup games for the Hammers.

In August 1956, he was appointed as player-manager of Clacton Town (where his brother Ken played in the side; he also played a few games for Spurs during the war) and spent 1959-60 with Romford. 

Interestingly, in the 1950s, Les had a cameo role in the film "39 Steps" starring James Mason.

He also came out of retirement in 1964 to play for the reformed "Push and Run" team for John White's Memorial Fund.

Les lived his latter years near White Hart Lane and used to be a regular visitor to the club on match days.

Died in St. Joseph's Hospice in Hackney on 29th April 1999