Dumfries born centre half David Calderhead played for Dumfries Primrose in 1904 and Maxwelltown Volunteers in 1905 before joining his father’s club (David Calderhead Sr), Second Division Lincoln City for the 1906-07 season, without appearing for their first team. He returned to Scotland before a second foray into English football, joining Second Division Chelsea, by now managed by his father, in 1910 and making his Pensioners debut in an FA Cup tie against Southern League club Leyton in January 1911. His Football League debut followed a week later in a home victory over Leicester Fosse.
He played 6 FA Cup ties in a run culminating in their semi final defeat to Newcastle United at St Andrew’s, Birmingham. However his first team opportunities were sporadic and after a single goal against Middlesbrough in November 1913 (Chelsea were by then in the First Division after promotion in 1912 as Second Division runners up) in 43 appearances for The Pensioners he joined Motherwell in the summer of 1914, for whom he played only once in 1914-15. After the First World War he joined Clapton Orient in 1919, making a single and final playing appearance against Wolves that September, before retiring and, following in his father’s footsteps, becoming manager of Lincoln City, a position he held from April 1921 to May 1924.
His father, David Calderhead Sr, played for Queen of the South Wanderers, Notts County and Lincoln City, and was a Scottish international. He managed Lincoln City from 1900 to 1907 and was most famously Chelsea’s manager from 1907 to 1933.