Alva, Clackmannanshire born left back John “Jock” Drummond had played for Falkirk between 1887 and 1892 before signing for Glasgow Rangers, for whom he made his debut against Leith Athletic in April 1892. He won five Scottish Cup medals (1894, 1897, 1898, 1899 and 1903) and four consecutive Scottish League Championships from 1899 to 1902, scoring twice in 223 appearances for Rangers during twelve years at Ibrox, forming a famous full back partnership with Nicol Smith.
Drummond was selected 14 times by Scotland between March 1892 and March 1903, winning his first cap while still at Falkirk in a 3-2 win over Ireland at The Solitude, Belfast. He captained his country on four occasions and also represented The Scottish League three times, all against The Football League, between April 1895 and March 1901. He finished his playing career with first club Falkirk, returning there in 1904 for three further seasons, latterly becoming their coach then, eventually, a director. He is notable for being the last outfield player in Scottish football to wear a cap while playing.