[2] The original school was based in disused wood and iron buildings which had previously been police barracks at the top of Canary Street in Auckland Park.

There were eighty-seven pupils in five Form II classes, four for boys and one for girls, with acting Headmaster, C. Hare.

He apologised for the lack of decent furniture and playing fields and promised that a new modern high school for boys would be built on the Parktown Ridge overlooking Milner Park and a new high school for girls near Zoo Lake.

On 1 September 1921 the school was divided into five houses: Romans, Spartans, Thebans, Trojans and Tuscans.

[3] More recently, Parktown has built Surgite House overlooking the McCorkell Oval (named after Neil McCorkell the school's former cricket coach and former Hampshire county cricketer who became a centurion in March 2012) to incorporate the administration and entertainment needs of Old Parktonians, as well as the Sydney Klevansky Sports and Cultural Centre.

[5][6] Parktown Boys' has a history which includes the use of boaters (called 'bashers'), a distinctive red and black uniform, school songs, and particularly 'Parktonian' language which has evolved over the years.

[11] The school has a weekly boarding establishment (i.e. from Sunday evening to Friday afternoon), which is known as the Druce Hall.

As part of their orientation and initiation into the school, all 'formies' (Grade 8/Form I) receive a coloured button to wear on their blazer which indicates their 'formie' status as well as what house they belong to for the duration of their Form I year.

[citation needed] Parktown conducts a Memorial Parade and Service on the Sunday nearest 11 November (Remembrance Day) every year for Old Parktonians and South Africans in general who have died in various conflicts around the world.

Every year in the first term Old Boys are invited to play against current school First Teams in a variety of sports.

The day culminates in rugby and hockey games between the Old Boys and the recently announced First teams.

[citation needed] Past matriculants of the school have gone on to be leaders in all fields of South African life, from leaders in commerce, Members of Parliament, renowned academics, Springboks rugby players, protea cricket players and other internationally renowned sportsmen, musicians and artists.

[32][33] On 15 January 2020, a 13-year-old pupil drowned while attending orientation camp at the Nyati Bush and River Break lodge, near Pretoria.

[34][35] The principal was subsequently reinstated after being cleared of any wrongdoing with the latest investigations being focused on Nyathi Bush and River Break lodge.