[3] In 1953, it was joined by Oakwood Technical High School for Girls in what became the Woodlands area of the building.

[4] The two technical schools were part of central Rotherham's tripartite system of secondary education.

South Grove and Spurley Hey secondary moderns, which were already 11–16 schools, also became comprehensives, though both have since closed.

In 1987, the neighbouring South Grove Comprehensive School closed, which extended Oakwood's catchment area further towards the town centre.

The school introduced vertical tutorship in September 2005, with forms organised into five houses named after trees: Aspen, Beech, Larch, Rowan and Willow.

A new uniform, consisting of grey (black for Year 11) jumpers/cardigans, white shirts and house ties, was also phased in.

Oakwood was used as a filming location for the BBC adaptation of David Walliams' Billionaire Boy, broadcast on New Year's Day 2016.

From 1992 to 2010, the school hosted the Oakwood Real Ale and Music Festival, which took place in the February half-term each year.

As Oakwood does not have its own sixth form, the majority of Oakwood's students embark on their post-16 education at the neighbouring Thomas Rotherham College for academic courses or Rotherham College of Arts and Technology for vocational courses.

A significant minority attend Wickersley School and Sports College's sixth form.

In November 2013, Oakwood transitioned to a Multi Academy Trust, to enable it to expand and support other schools.

The Multi Academy Trust was initially known as the Oakwood Learning Community In June 2014 one of its feeder schools, Sitwell Junior School, joined the Multi Academy Trust with David Naisbitt as the Accounting Officer.

By October 2017, the Inspire Trust had grown further, with the addition of the Thomas Rotherham College, which dissolved the Corporation of Thomas Rotherham College, reopening as a 6th Form Academy, within the Inspire Trust family.