[7] In 1993, Highland Regional High School students voted to allow a prayer before their graduation ceremony.

The school district was quickly sued by a graduating senior with the support of the American Civil Liberties Union of New Jersey over separation of church and state.

The case was heard by the United States Court of Appeals for the Third Circuit, which ruled against the school district in a 9-4 decision.

[17] The 1975 baseball team finished the season with an 18-7 record after winning the Group I state title by a score of 1-0 against Ridgefield Park High School on a one-hitter in the championship game.

[22] The program produced one of the greatest wrestlers in New Jersey history, Joe Melchiore, who lost only three matches his entire career, all during his freshman year.

In the Group IV state meet, the top five runners finished 3rd, 5th, 20th, 23rd, and 36th to win with 67 points, ahead of the second-place team, Westfield High School, which scored 92.

The band successfully defended their Chapter One Championship in 2006, and were the 2002 Atlantic Coast Invitational Champion in Group 1.

[28] The school's pep band performs in numerous parades winning first place at the Bridesburg Memorial Day Parade in 2012 and 2013 The school's indoor color guard was the Tournament Indoor Association Scholastic Novice champions in 2006 and the Scholastic Intermediate A champions in 2007.

The school's competitive jazz ensemble placed second in the New Jersey state finals in 1991 and first in the Atlantic Coast Championships in 2013 and 2014.