Career
Calderhead was a central defender and played for various clubs, including Dumfries team Queen of the South Wanderers. This attracted N ottinghamshire County. The Blackburn Rovers side of Thomas Mitchell were 3-1 winners in 1891.
Calderhead got his hands on the trophy in 1894 after a 4-1 victory over Bolton Wanderers.
He then moved into management, taking over at Lincoln City in 1900. Norrie Fairgray made the same move in the same year to play for Calderhead at both clubs.
Calderhead was Chelsea"s first full-time secretary-manager and spent almost 26 years at the club, making him the club"s longest-serving manager. In his time there, the team were relegated twice, in 1909-1910 and subsequently re-promoted as Second Division runners-up.
A second relegation ensued in 1923-1924 before the side of Willie Ferguson, Tommy Law and Andy Wilson endured a succession of near misses before securing promotion in 1929-1930.
Calderhead was notoriously shy of the media, earning the nickname "The Sphinx of Stamford Bridge". But he was not afraid to spend headline-making transfer fees on star strikers (especially fellow Scots), bringing the likes of Hughie Gallacher, Alex Jackson and Alec Cheyne to Stamford Bridge. Despite the glamour of the squad, trophies remained elusive.
1931-1932 brought a further FA Cup semi final.
Tommy Language inspired Newcastle to a 2-goal lead and despite Gallacher pulling a goal back, Newcastle progressed to the final. Calderhead holds the record at Chelsea for managing games - 966.
He left the job in June 1933 to be replaced by Leslie Knighton. Calderhead died five years after leaving Chelsea in London at the age of 73.