The school was established in 1582 as Kirkcaldy Burgh School; the "High School" name dates from the middle part of the 19th century. The school's motto is Usque conabor, "I will strive to my utmost". The High School was originally on St Brycedale Avenue and part of the old building is now incorporated into Kirkcaldy College. In 1958 a new school was built on Dunnikier Way in the shape of a 'H' and opened by the Queen. In 1970 the last entrance exams for the school were taken after which pupils were zoned into their nearest high school. The following year Templehall High School became the "Junior" building of the High School originally accommodating 1st, 2nd & 3rd year pupils. The original high school became home for the seniors. As requirements changed over the years the senior school was extended and pupil numbers declined. The requirement for two buildings was no longer necessary. In 1994 the junior building was closed and demolished; the site is now occupied by a housing estate. The most recent inspection of the school took place in 2012. The reports stated that the school was making good progress with its goals and identified key strengths: pupils who were proud of their school and positive about learning, high achievement in out-of-class learning, high quality pastoral care, very good community partnership working, staff who listened to and involved pupils, and the headteacher's leadership of an improving school. In March 2014, the school won the prestigious COSLA Excellence Award for its work in relation to teenage sexual health and pregnancy prevention. Working with NHS Fife, the school was recognised as being an example of best practice in this field and was featured in the national press, TV and radio. Later in 2014, Kirkcaldy High School was shortlisted as a finalist in the Scottish Education Awards 2014 in the Health and Wellbeing section and were selected as the "Kingdom FM" Best School in their "Local Hero" Awards in August 2014. During session 2015-2016, the school was increasingly involved in promoting "STEM" Education, with a staff member being recognised as UK STEM Teacher of the Year, the school winning the Scottish finals of the Engineering Development Trust's "Go4SET" competition and another finalist place in the Scottish Education Awards In 2018, the school won a second COSLA Excellence Award for their work tackling LGBT+ bullying and promoting equality across the school as well as taking training to a number of local and national organisations. In 2020, the school was awarded "Gold" status as a UNICEF "Rights Respecting School".
House system
The pupils of Kirkcaldy High School are organised into four different houses. Originally the House system was named after areas of Kirkcaldy - Balwearie, Raith, Ravenscraig & St. Serfs. Now the houses are named after famous persons of the town.
Oswald - Named after an old Kirkcaldy family, at one time associated with the Dunnikier estate, on which the school is now sited.
Adam Smith - Named after the famous economist who wrote ''"The Wealth of Nations" and attended the school in the eighteenth century.
Carlyle - Named after the famous writer Thomas Carlyle who famously wrote "The French Revolution, A History" and taught at the school between 1816 and 1818.
