[2] Once a large independent city, Oakleigh was absorbed into Melbourne as part of the eastward expansion of the metropolis in the 1950s.

The area is traditionally known to have a strong Greek cultural influence, largely due to the influx of immigrants to Australia in the mid-20th century.

[4] Originally inhabited by the Kulin people, a grazing run was established in the settled district east of Melbourne in the early 1840s, for which the lease was taken up by farmers John and Archibald McMillan.

Oakleigh's urban potential was increased by the addition of part of Caulfield, comprising present day Hughesdale, in 1913.

[4] The Convent of the Good Shepherd occupied the northernmost boundary of the city until it was demolished in 1984 to make way for the extensions of Chadstone Shopping Centre.

Chadstone Shopping Centre opened in 1960 and was constructed on land that was initially leased from the Good Shepherd Sisters for 99 years.

Although trading in the three or four active street in the Oakleigh shopping centre was maintained with one-way traffic and pedestrianisation, the contrast with climate-controlled Chadstone was apparent.

In 2011, a Performing Arts Centre was added, it being built out of concrete and having an iron roof, and in 2017, portable classrooms were placed on the tennis courts to cater to the ever-expanding school.

The motel ushered in an era when the motor car dominated the city as Melbourne sprawled and expanded to absorb Oakleigh and also Dandenong into its ever-expanding south-eastern conurbation.

The area is traditionally known to have a strong Greek cultural influence, largely due to the influx of said immigrants to Australia in the mid-20th century.

This area contains many older commercial buildings including banks and retail complexes dating back to the early days of the city.

Eaton Street is a pedestrian mall which connects Atherton Road with the Centro Shopping Centre and railway station.

The CBD is a popular activity centre with locals with a great many cafes, several hotels, restaurants and retail shops.

An association football club, the Oakleigh Cannons FC, competes in the Australian second-tier competition, the National Premier League.