The school was built for the 1960-1961 school year. In 1970 an addition to the school created a second gym, now known as the new gym, and a new wing. The additions in 1978 and 1986 added on wings, an auditorium, and expanded the
library. Woodlawn High School's unofficial rival school is
Dartmouth High School. Woodlawn High School celebrated its 50th anniversary in 2010, when its 50th class graduated. Formerly named in honour of
Prince Andrew, Duke of York, the school was reported in 2019 to be considering a name change due to his allegations of sexual abuse, and because the name "no longer reflects the values of the community." In June 2022, the school was renamed to 'Woodlawn High School'. ==Fine arts==