It is believed to be the oldest road in Toronto, starting as a native trail called "old portage" along the shoreline scarp of Glacial Lake Iroquois.

The trail, which continued along the modern route of Kingston Road east of the Don, and what is now Dundas Street west of the Humber.

During the 1837 Upper Canada Rebellion rebel leader William Lyon Mackenzie personally burned the home of Dr. R. C. Horne a prominent Tory, at the corner of Davenport Road and Yonge Street.

[6] On April 20, 1891, the newly incorporated Davenport Street Railway Company was awarded rights to operate a streetcar by West Toronto Junction.

[8] The line had originally used a broad gauge, like Toronto's other streetcar lines—so railway companies couldn't run freight on ordinary streets.

In 1896, The Daily Mail and Empire published a letter from a reader responding to recent article on roads requiring repair in Toronto described Davenport as being in "simply disgraceful condition".

In 1912, the farm at the south-west corner of Bathurst Street and Davenport became the Hillcrest Racetrack of Abe Orpen.