[3] The original school building opened in 1925, designed by architect William Bunker Tubby in the Colonial Revival Style.

[7] Between 1970 and 1971, the original, Tubby-designed 1920s school building was demolished and replaced by the current structure, designed by Caudill Rowlett Scott.

[11] The publication of the article in the school's newspaper triggered a full-scale investigation that found officials had embezzled $11.2 million from the district over 8 years.

[12][13] Former Roslyn student Mike Makowsky dramatized the scandal in the 2019 HBO film Bad Education, starring Hugh Jackman as Tassone and Allison Janney as Gluckin.

[15] In the summer of 2017, the district embarked on a major renovation project at the high school, as part of a district-wide modernization initiative.

[16] This renovation included completely gutting and renovating the first floor hallways, demolishing, replacing, and expanding the library, constructing an additional gymnasium, installing air conditioning in the world language and math/2nd floor science hallways, reconfiguring the front circle and constructing an entrance plaza (including an awning and vegetation) and security vestibule, expanding and resurfacing the faculty and student parking lots by relocating the district's bus garage to an area adjacent to one of the elementary schools, and creating a student lounge next to the school store.

[20] Additionally, the center of the front circle would remain the home for one of the marble horse tamer statues from the Mackay estate, which was restored and re-dedicated on October 10, 2019.

After the Mackay estate was demolished, the statue that now resides at the high school was forgotten, only to be stumbled upon years later by a local artist, George Gách.

[18][19] The re-dedication ceremony for the restored Horse Tamer statue took place in the front circle of Roslyn High School on October 10, 2019.