As in other neighborhoods, the names of many streets in the Oakland area derive from families of early landholders. Some of these which survive on present day streets are January, Dalton, Devlin, Wise, Tamm, Kraft, Berthold, Prather and McCausland. Ones which have fallen by the wayside include Cooper, Woods, Billon, and Davis.

In the 1830's, the Sublette brothers, William and Solomon, each purchased a large tract of land with profits from their successful fur trade ventures. These tracts were in the eastern part of Gratiot League Square along Kingshighway, south of Manchester. William, the elder, married Frances Hereford and upon his death in 1845 he willed his fortune to his wife providing she did not change her name. So as to protect her interest, she subsequently married her brotherin-law, Solomon. After her death in 1857, the tracts were subdivided and one was platted as Fairmont in 1868. Streets hearing their family names now run through the area. A name which formerly applied to West Park Avenue and to portions of Sublette and Sulphur Avenues, was Cheltenham. This name was once given to an area also known as the Sulphur Spring Tract and to a local station on the Pacific Railroad. It originated as the title of the country estate of William Wible and was taken from a well-known spa in Gloucestershire, England. Cheltenham later survived in the name of a clay products company along Manchester Avenue, but is not presently used in that vicinity.

Sulphur Avenue takes its name from a sulphur spring near the River des Peres, located on David W. Graham's large tract of the same name. Manchester Avenue was originally called Fox Creek Road, but was later given its present name because it was the route to the town of Manchester. Clayton Road, was so-named because it ran out to the country estate of Ralph Clayton, later to become the county seat. Oakland:Avenue received its name from the many oak trees in adjacent Forest Park. Macklind Avenue is named for a surveyor and engineer who laid out subdivisions in the area, as was a street named Cozens, which is now a portion of January Avenue. Hampton Avenue was originally the western most street in the Southampton Subdivision and when the street was extended in the 1920's, that same name was continued on portions of Billon and Sulphur Avenues to create a continuous street.

Many street names are attributable to the subdivisions in which they were situated. Examples of these in the Oakland area includes Glades, Victoria, Dillenberger, Ellendale, Forest and Blendon. It is interesting to note some of the former names of present day streets such as Dale Avenue, which was Valley Road, Mitchell Avenue was Hill Road, Graham Street was Center Road, a part of Wise Avenue was Plateau and Barron Avenue was Gratiot Road. Finally and obviously, League Avenue perpetuates the memory of the Gratiot League Square.