A talented half-back in his younger years, Grimsdell spent the majority of his playing career with Tottenham Hotspur whom he first joined in 1912. His occupation was interrupted by the Great War soon after, during which time he served with the 1st Regiment of Life Guards.
Following the Armistice and return of the Football League, Grimsdell was appointed captain at Spurs and soon guided them to win both the Second Divison (1919-20) and the FA Cup (1920-21). He would remain with the North London club until the close of the 1928-29 campaign. During the summer break, Grimsdell decided to take his first step into management, joining the O’s, who had just suffered the first relegation of their history and found themselves in Division Three (South).
Unfortunately, a difficult started ensued and when Christmas morning arrived, Orient sat fifth from bottom in the league having achieved a meagre two wins all season. By this time, Grimsdell’s much delayed registration had been approved by the FA and he drafted himself into the side, playing a total of seventeen games in all competitions that season, scoring two goals.
Both goals came in the FA Cup, which provided some much needed optimism for the club; they achieved only their third fourth round visit to date, bowing out to top tier Newcastle United on 25th January. In the first round, two replays had been needed to eliminate non-league Folkestone Town. The second replay took place at Arsenal’s Highbury in front of just 3,500 spectators, as Grimsdell found the scoresheet in a 4-1 victory.
The O’s form improved after their exit from the FA Cup and they obtained safety with a twelfth place finish. However, over the summer, Grimsdell resigned as manager and was soon replaced by his predecessor Peter Proudfoot. Grimsdell would not enter football management again, but would later serve on the board of directors at Watford.
