The earliest records of James John Bentley's involvement with Manchester United date back to 1903 when he was chairing meetings of the board of directors. Here his name regularly signs the minutes of the board meetings, and continues to do so until December 1908.

Bentley became a shareholder of the club with ten ordinary shares as of the 26th November 1907. These shares were allocated when the Club became a Limited Company.

During this time he was also controller of the Lancashire FA and served on the committee of the Football League from 1888 to 1893 and 1910 to 1912; he became vice president in 1893-94; President from 1894 to 1910; and a life member in 1912.

Following the departure of Walter Crickmer - who was brought to the club in the first place by Bentley - it was natural for the man who had held such high positions to take the helm of the club as manager.

In his two seasons as manager Bentley guided United to fourth in the first season and 14th in the second. This patchy form and rumours of his style of management upsetting some of the senior players led to his resignation as manager and return to his original role of club secretary.