Dulwich College had been playing football using Rugby School rules since 1858 and the school had been playing against scratch sides of old boys since the 1890s. In October 1897 a former pupil of Dulwich College wrote to the school magazine ("The Alleynian") bemoaning the fact that despite the school having an old boy representative ""in almost all the first-class football clubs"" the fact that it did not have an old schoolboy team, ""such as Old Merchant Taylors, Old Leysians, Old Carthusians, Marlborough Nomads"", meant that it was missing out on ""the greater athletic reputation would otherwise have obtained."" Within a few months R.M. Everett, a member of the school's first XV, and William Leake, an Assistant Master at the school and former Cambridge rugger Blue, had joined forces to promote the formation of the club. In June 1898 Leake published an invitation in ""The Alleynian"" to ""all OAs desirous of joining"". In September 1898, the club played its first match, drawing with Croydon 3rds (Croydon FC being the name by which Old Whitgiftians were known at the time). On 8 October 1898, the club's first general meeting was held, rules approved, officers elected and the dark blue, light blue and black hooped jerseys were decided upon.