Cleveland Street was the original route of the Roxboro-Fayetteville road, which, from Main Street (the Hillsborough-Raleigh Road) wended north on Church Street, around the Trinity Methodist Church, and northward. By 1881, the blocks south of where present-day Seminary intersects (then Hutchins, later Wyatt) were called "Person Street" (as in the County) and the blocks north Roxboro Road. By 1887, the entire section between Church and Mangum Street has been renamed Cleveland Street after Grover Cleveland (per Wyatt Dixon,) who had been elected POTUS in 1885.
The southern blocks of Cleveland Street were completely screwed up by the downtown Loop, so that Cleveland no longer connects with the downtown street grid, accessible only from the one-way west Loop. The remnant of the intersection with Church Street and Liberty Streets (also severed) remains as a kind of driveway next to Trinity Methodist Church.