A pacy winger, who had a good delivery, Charlie Woodruff spent two seasons at Tottenham.

Beginning his career in the Midlands League with Grantham Avenue, Woodruff moved to Tottenham on 14th March 1908 with the player being given the maximum signing on fee at the time of £10.  A week later, his first Spurs game came in a 2-2 draw at Sittingbourne, with his first first team game being even more notable, as he scored two goals in a 5-2 victory over Leyton in the Southern League.   With five goals in five games up to the end of the season, he cost Spurs another £20 for making a set number of appearances.

His presence in the first team cost Tottenham £20 as his transfer had included an appearance trigger for the money to be paid to his first club. 

The following season in the Second Division of the Football League, Woodruff played eight games and scored once - against West Bromwich Albion, then featured in two games in the First Division in the following season.  He also played in the reserves, scoring six goals in 57 games in the South Eastern League, before he was released in August 1910.

The rapid promotions perhaps caught Charlie out and at the end of the 1909-10 season, he was allowed to return to the Midlands League with Doncaster Rovers and later the winger played for Grantham FC for a while.

Charlie Woodruff died in Grantham on 17th July 1943.