He was born in Watford, Hertfordshire and played at centre-half and later wing-half for Tottenham Hotspur and England.

Grimsdell started his career at St Albans City[2] and Watford but transferred as a schoolboy player to Tottenham Hotspur at the age of 18 in April 1912.

[4] On his return in 1919, he captained Tottenham and scored 14 goals in the 1919–20 season,[3] and led the team to win the Second Division that year.

In recognition of his distinguished career and service to the club he was admitted into the Tottenham Hotspur Hall of Fame.

[6] Following the conclusion of the Second World War, Grimsdell served on Watford's board of directors from 1945 until 1951.