[1] The original Caldwell High School was built in 1910, at which time it served students from Essex Fells, Fairfield Township, Hanover Township, Livingston, North Caldwell, Roseland and Verona, who attended as part of sending/receiving relationships with their home school districts.

[10] James Caldwell High School's teams, nicknamed the Chiefs and Lady Chiefs respectively,[2] compete in the Super Essex Conference, which is comprised of public and private high schools in Essex County and was established following a reorganization of sports leagues in Northern New Jersey by the New Jersey State Interscholastic Athletic Association (NJSIAA).

[13] The football team competes in the National White division of the North Jersey Super Football Conference, which includes 112 schools competing in 20 divisions, making it the nation's biggest football-only high school sports league.

[16] The school has had past successes in its football and baseball programs, and has been a perennial contender in girls' volleyball and softball.

The 1981 team finished the season with an 11-0 record, marking the first time the program completed a season unbeaten, after winning the North II Group III state sectional title by scoring 17 unanswered points for a 17-6 comeback win against Rahway High School in the championship game.

[23] The team then beat Rumson-Fair Haven Regional High School by a score of 18-14 at SHI Stadium to become the first ever overall Group II champions and extend their winning streak to 28 games, the longest in the state.

[28] The team was a sectional winner for the third consecutive time in 2005 with a 2–0 win against Governor Livingston High School in the tournament final.

The 2005 team finished the season with a record of 32-1-1 after winning the Group II title by a score of 3-2 against Audubon on a walk-off home run in the seventh inning of the championship game.

[35] The program has produced 10 NFCA All Americans: Gina Capardi and Kristen Schindler 2005, Desi Giordano 2007, Paige Johnson 2009 and 2011, Gabby Roselle 2012, Gianna Genello 2014 and 2015, Nicolette Luzzi 2018 and 2019, and Caitlin Cetrulo, Carina Whiting and Michayla Rodriguez 2021 3 Chiefs were named to the Star-Ledger's first team All State All Groups: Jen Luker 1992, Kristen Schindler 2005 and Gina Capardi 2005 The James Caldwell girls' volleyball team has won six state titles under Jeff and Scott Stiefbold, winning Group II titles in 2000, 2002 and 2003 (all against Union Catholic High School in the final match), in 2004 (vs. Pascack Valley High School) and in 2009 (vs. Tenafly High School) and took the 2008 Group I championship with a win against Bogota High School; the six state titles are the ninth-most for any school in New Jersey.

[37] The boys' tennis team had one of their most successful years in 2011, led by then senior captains, Ethan Flint (14-6 record) and Andrew Lucila.

The senior class of 2012 featured a trio of four-year starters in Dylan Silver, Neil Shulman and Michael Melchione, who became the most successful senior class in the history of Essex County tennis, posting an overall team record of 52–22 over the four-year span.

Individually, Neil Shulman finished with a personal record of 52–14, the most wins by a singles player in Essex County history.

In 2019, the boys' team advanced to the semi-finals of the Essex County Tournament for the first time since the tournament's inaugural year in 1974, defeating fourteenth state-ranked Millburn High School in the quarterfinal, eventually losing to Montclair High School 1–0 in the semi-final.

Teshkoyan was named by The Star-Ledger as NJ's Girls' Soccer Coach of the Year in 2008 guiding the team to an 18-4-1 mark.

The 2003 team won the Northern Hills Conference Championship with an upset victory over perennial power Morris Catholic 3-2 and finished with a 18–5 record.

[46] Most scenes of Welcome to the Dollhouse were filmed at James Caldwell High School, including the cafeteria, hallways, classrooms, the bathroom, and the principal's office.