[2] The high school was established in 1903, operating on the top floor of a two-story building that served grades 1-12.

A referendum was held in 1959 on the construction of a new high school to be located on a plot of land bordering Eyland Avenue.

With a growing student population across the township, a new building was constructed adjacent to the existing high school on land bordering Hillside Avenue and opened on September 6, 1972 [8] In 2017, the district brought on former Roxbury Chief of Police, James Simonetti, to serve as the Director of Security to improve safety procedures.

This included the addition of man-traps, upgraded security cameras, revisiting policies and procedures, as well as improving the vetting of visitors.

In addition, there are nine select group choirs, a variety of wind ensembles, and two marching bands that allow students to pursue interests beyond the school day in the co-curricular domain.

“Bronze certification means a school has made a commitment to sustainability and succeeded in implementing significant first steps, while silver certification means a school has made significant progress in a number of categories toward sustainability and is a statewide and national leader”.

[1] In 2005, Roxbury performed "The Music of Scheherazade", and placed 4th overall at the United States Scholastic Band Association (USSBA) All-States Championships at Giants Stadium with a score of 96.48.

[18] The band won the state championship in the Group IV Open Class in the 2015 competition held at High Point Solutions Stadium.

[30] The 1992 team finished the season with a 24–5 record after winning the Group IV title by defeating Middletown North by a score of 3–2 in the championship game.

[31] The 2021 team finished with a 20–7 record, winning the North I, Group III Sectional Championship against Passaic Valley High School.

[34] The girls soccer team won the Group IV state championship in 1997, defeating Eastern Regional High School in the final game of the playoff tournament.

[42] The first Roxbury football team was formed by students in 1913 and lost their first game to Newton High School by a score of 7–0.

1987 was the senior season of Dave Moore '88, a future NFL pro-bowler, whose #88 became the team's first number to be retired.

[46] 2002 marked Head Coach Cosmo Lorusso's first year in Roxbury, when the Gaels made the sectional semi-finals and finished as IHC-Iron Tri-Champions.

The 2009 team jumped to an 8–0 start, quickly winning the inaugural Northwest Jersey Athletic Conference-American Division championship.

[47] In 2012, the Roxbury High School Football Gaels played their 100th season of football, celebrating it with an 11–1 season and the program's sixth state championship with a 14–6 victory over Pascack Valley High School in the North I Group IV finals at Kean University.