A group of prominent educators, including Anton Methfessel of the Methfessel Institute, founds the Staten Island Academy and Latin School on September 5, 1884. 

The Academy gains national prominence with its progressive curriculum, ushering in an era of rapid expansion. Subjects for years 9-12 include Latin, German, French, English, geography, physiology, zoology, mathematics, history, natural philosophy, expression, music, and drawing. The Academy builds associations with luminaries across multiple disciplines, including actor Sidney Wollett, North Pole explorer Admiral Peary, Booker T. Washington, the Vanderbilt family, Jacob Riis, and George William Curtis, the namesake for Curtis High School.

The school purchases land at the corner of Wall Street and Academy Place in the St. George section of Staten Island. A new building is built to accommodate a growing student population, with the cornerstone placed in 1895. This marker now stands outside Alumni Hall on the Todt Hill campus.

The Academy adopts cutting-edge educational pedagogies, including those championed by John Dewey and Friedrich Froebel, the creator of the Kindergarten. Physical education gains emphasis alongside academics, with the Academy offering football, ice hockey, track and cross-country running, basketball, baseball, tennis, and shell-racing.

Renowned critic and arts patron William Winter establishes the Winter Memorial Library at the Academy in memory of his late son Arthur. Modeled after Sir Walter Scott’s, the library includes autographed portraits of Dickens, Gladstone, and Disraeli, and holds first editions of Twain, Dickens, Johnson, Byron, Andrew Carnegie, and Bram Stoker. The library receives national renown.

The Academy acquires and merges with several other schools, including the Livingston School, a highly regarded progressive elementary institution, the Dongan-Hall Arden School, and the Willard-Mundorf School.

The Lower and Middle Schools of the Academy move to Dongan Hall, a Georgian mansion formerly belonging to Edward Stettinius, Secretary of State for both FDR and Truman. The Upper School remains at the Wall Street campus.

The Academy begins an expansion of the Todt Hill campus, building facilities to house the entire school. The additions include the Early Childhood Building, Kearns Hall, and the O.J. Buck Gymnasium, which are still in use today.

Alumni Hall is completed, and the entire student body is moved to the Todt Hill campus.

A fire destroys Dongan Hall, the jewel of the Todt Hill campus. The building is irreparably damaged, and most of the Winter Memorial Library portrait and book collections are lost. A single remnant from Dongan Hall, a pendulum clock, is saved.

Crowe Hall is built on the site of the Dongan Hall building, and houses the Patrick Commons dining hall, the Head of School's office, and administrative spaces. A sister structure, Haugen Hall, home to the auditorium, Stanley Library, and arts classrooms, is also completed.

The Academy reaffirms its commitment to cutting-edge education with the addition of the Francis H. Powers Science and Technology Center. Other notable facilities include two outdoor swimming pools, tennis courts, athletic fields, and the Art Barn, used for Lower School art classes.

Extensive renovations are underway. The Academy refurbishes the Stanley Library, upgrades the Patrick Commons dining hall, and installs new playground equipment. With support from the Parents’ League, a new fitness center opens in the fall.

The Academy begins restoration of the school's athletics fields. This project is generously funded by The Alexander Robbins Steinman Foundation in honor of Alex, class of 1986, who died on September 11.

A Memorial Fund dedicated to Nancy B. Avis, a 1986 Advance Woman of Achievement and ardent supporter of the Academy's sports teams, supports extensive improvements to the O. J. Buck Gymnasium. These include updates to the training room and the gymnasium floor, new electrically operated folding bleachers, and a rock-climbing wall. The Academy also makes data center and technology updates, improving IT functionality while reducing energy consumption.

The technological updates continue. The Patrick Academic Resource Center (PARC) opens its doors, offering an all-ages study space equipped with supplies, laptops, iPads, printers, and SMART boards.

On May 30, 2015, Staten Island Academy dedicated a memorial arboretum to NYPD Officers Rafael Ramos and Wenjian Liu, who were tragically killed in the line of duty. Officer Ramos' son Justin graduated from the Academy in 2013. Members of the Class of 2013, 2014, and 2015 contributed significantly to the memorial's funding.

Students learn in state-of-the-art facilities on a lovingly tended 12-acre campus. Today's Academy remains dedicated to the ideals of fostering intellectual excellence, compassion, and creativity, while rising to meet the unique challenges and interests of the modern world.