It is quite probable that the street was named after John Sayle who owned land between the Catholic Church and King Street. In June 1891 he purchased the land from William Herbert, being lots 22, 24, 26 on the plan of subdivision 2566, Crown Allotment 9 in the parish of Burgoyne County of Evelyn. These blocks approximate to the current street numbers 6-10 at the bottom of the hill.

Until the 1970s the section between King Street and the Roman Catholic Church was merely a road reserve with not even a wheel track. In the winter time the area at the bottom of the hill was a swamp.

Apart from the Catholic Church which was built in 1890, the other public building in this street was the town's second police station. It stood on the corner of Oliver and Sayle Street from about 1890 until 1944. The old stables (much modified) still stand at the rear of the site.

Sources: Yarra Glen and District Historical Society Newsletter, no.17, August 2007