[2] He won one Scotland cap, in a 7–0 win against Ireland at the first Ibrox Park in the British Home Championship in March 1889; this attracted Notts County.

With Notts County he played in two FA Cup finals:[3][4] the Blackburn Rovers side of Thomas Mitchell were 3–1 winners in 1891,[4][5] but Calderhead got his hands on the trophy in 1894 after a 4–1 victory over Bolton Wanderers.

In leading his side to a shock replayed win over Chelsea in the first round of 1906–07 FA Cup, he impressed the west London club's board enough for them to appoint him manager later that year.

The 1919–20 season was Chelsea's most successful under Calderhead, finishing 3rd in the First Division and reaching the FA Cup semi-finals, where they lost to Aston Villa.

[7] Nevertheless, The Times described him as "one of the managers who started the fashion of paying huge transfer fees and was responsible for bringing many celebrated players to Stamford Bridge, including [Hughie] Gallacher and [Alex] Jackson.