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For the 1992-93 school year, Montgomery High School was awarded the National Blue Ribbon School Award of Excellence by the United States Department of Education, the highest award an American school can receive.
In the 2011 "Ranking America's High Schools" issue by The Washington Post, the school was ranked 13th in New Jersey and 636th nationwide. The school was ranked 643rd nationwide, the 18th-highest in New Jersey, in Newsweek magazine's 2010 rankings of America's Best High Schools. In Newsweek's May 22, 2007 issue, ranking the country's top high schools, Montgomery High School was listed in 656th place, the 13th-highest ranked school in New Jersey.
The school was the 33rd-ranked public high school in New Jersey out of 339 schools statewide in New Jersey Monthly magazine's September 2014 cover story on the state's "Top Public High Schools", using a new ranking methodology. The school had been ranked 61st in the state of 328 schools in 2012, after being ranked 10th in 2010 out of 322 schools listed. The magazine ranked the school 16th in 2008 out of 316 schools. The school was ranked 4th in the magazine's September 2006 issue, which included 316 schools across the state.