In 1895, a school building was erected in the neighborhood of Stapleton at the corner of Broad Street and what is now Wright Street. This school, Public School 14, was later moved to 100 Tompkins Avenue-not too far from the original 
site. Shortly after the school was moved, in 1947, the City of New York decided that they wanted to create a playground for Public School 14. By 1951, P.S. 14 Playground opened under the jurisdiction of the New York City Department of Parks and Recreation and the New York City Board of Education.
When P.S. 14 Playground first opened, it was divided into three sections. The first section had a comfort station, a rack for bicycles, a sand pit, seesaws, slides, swings, and a wading pool. The second section housed basketball courts, exercise equipment, paddle tennis courts, shuffleboard courts, volleyball courts, and more slides and swings. The third section just had handball courts. Scattered amongst all of these recreational facilities were benches, a drinking fountain, and a flagpole.
By the end of the twentieth century, the New York City Department of Parks and Recreation decided to rename many of Staten Island's parks. In 1996, the commissioner of
 the New York City Department of Parks and Recreation changed the name of P.S. 14 Playground to Stapleton Playground. Since then, many renovations have been done to the park. Stapleton Playground now has many more recreational facilities, including baseball fields, a mini pool, a bird-shaped spray shower, and a tic-tac-toe board.
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