Before Roger Ludlowe Middle School opened up on campus in 1998, Fairfield Ludlowe High School was a middle school and all the middle school students went to Fairfield Warde High School. FLHS was reopened as a high school in fall 2003 because of overcrowding at Fairfield's one existing high school, now called Fairfield Warde High School. The school was originally opened as "Fairfield High School at the Ludlowe Site," as a satellite campus of Fairfield High School housing 9th and 10th grades. In Fall 2003, The Board of Education decided that it would be called Fairfield High School South, while the existing high school would be called Fairfield High School East. The board claimed that they voted for these names to minimize rivalry between the schools. Several months later, after much persuasion, the board voted to change the name of the two schools to Fairfield Ludlowe and Fairfield Warde, keeping the names from before the 1987 consolidation but also maintaining the reputation of the Fairfield name. There now exists a healthy rivalry between the two schools. The two schools frequently compete in sports games and academic trivia.
In 2012, the school debuted in the rankings for the U.S. News & World Report Best High Schools ranking. It is currently ranked as the 16th best high school in Connecticut, and the 527th best in the nation. The high school holds high expectations of its students in order to prepare them for rigorous post-secondary education. A majority of students who attend Fairfeld Ludlowe High School graduate and then attend highly ranked Colleges or Universities.