It was established in 2015, following the 2013 merger of Orillia District Collegiate & Vocational Institute and Park Street Collegiate Institute, and has a population of about 1,200 students as of the 2021–2022 academic year.

[2] The school building was built between 2014 and 2016, and is equipped with a triple gymnasium, technology rooms, a library, and cafeteria.

[3] After the 2012–2013 academic year, Orillia District Collegiate & Vocational Institute was merged with Park Street Collegiate Institute, which after declining enrollment, was demolished so that a new school could be built on its former site, at the intersection of Park Street and Collegiate Drive.

[4][5][6] In early June 2024, the school flew the Progress Pride flag in order to comply with a request from the Simcoe County District School Board's diversity, equity, and inclusion (DEI) department.

One OSS student who identifies as bisexual and transgender started a petition to replace it with the Canadian flag again, stating the decision "led to an increase in bullying of students from the 2SLGBTQ+ community".