Prior to the school's establishment in 1937, Pearland students had to attend secondary school in Webster. The first graduating class in 1938 included valedictorian was Beatrice Woods who would become Beatrice Woods Theriot after marrying Melvin Theriot. The original Pearland School, opened in 1937, had a staff of about 12 people and served 58 students in 1st through 12th grades on Grand Boulevard. In 1953, the campus moved to Galveston Avenue, and the Grand Boulevard school became Pearland Elementary. In 1991, the high school moved again, to Main Street. The Galveston Avenue property is now home to the Pearland Historical Society, a Brazoria County Tax Office annex, Pearland Junior High School West Campus, and Leon H. Sablatura Middle School. The school's mascot is the "Oiler Man" or "Oiler". In contrast to the local legend, the mascot was not inspired by the Houston Oilers professional football team. Instead it is a tribute to an important sector of the local and regional economy. Several local businesses in Pearland are related to the oil industry, including a helicopter service that ferries people to nearby off-shore oil wells in the Gulf of Mexico. The current Pearland High School campus opened in 1991, on South Main Street. The original building has a capacity of 2,200 students. The building houses the auditorium, 2 gymnasiums, several vocational trades shops, and the athletic locker rooms. In 1998, a 1,750 student capacity building was built adjacent to Pearland High School. This building houses three gymnasiums, a teaching theater, a broadcast studio, and a large cafeteria. This building was called the "North Campus" until being renamed for the late Sheryl Searcy, a longtime reading teacher at Pearland High School in 2009. Glenda Dawson High School opened in 2007, relieving the overcrowded Pearland High School. The school's marching band performed in the 2020 Rose Parade in Pasadena, CA on New Year's Day.
During the 2010 Football season, the Pearland High School football team had a perfect 16–0 record and upset the Euless Trinity Trojans in the Texas 5A State Football Championship. Notable athletes on the team include QB Trey Anderson, RB Dustin Garrison, DE Samuel Ukwuachu, and LB Kendall Ehrlich. The football team returned to the state championship game in 2013, but lost to the Kyler Murray led Allen Eagles in a blowout. On October 3, 2014, its football team defeated the Dawson Eagles. This was the first year that Pearland and Dawson has ever played each other in a football game.
