After the freeze of 1895, by careful management, money was saved and the first county high school was erected.

At a contract price of $5,100 (equivalent to $187,000 in 2024), a well-planned, two-story wooden building with science laboratories, a library and an auditorium was built large enough to accommodate as many as 250 high school students.

One of the oldest traditions is the wearing of red and black, the school's colors, every Friday to show spirit and unity.

The names of Hillsborough alumni, who were killed in action during the war were placed on a plaque under the tower.

The bronze terrier that guards the trophy case was originally placed in the courtyard by the Class of 1958.

HHS students from different graduating classes raised the funds, providing the stained glass windows in the auditorium in 1963.

"Harvard on the Hill" stems partly from the fact that Hillsborough High School was built on one of the highest geographical elevations in Tampa, had graduated many illustrious people, and emulated many of Harvard's traditions with regard to its alma mater and school color scheme, a crimson shade of red and black, and the big letter H. Historically, the colors red and black represent heart and soul.

Later, Hillsborough High also picked up the nickname "Peyton Place," probably sometime in the late 1960s or early 1970s, because the opening scene of the tower in the popular Peyton Place television soap opera somehow reminded some individuals of Hillsborough High's clock tower, and also because as one teacher put it, "it seemed there was always some sort of soap opera going on at the school."

On September 5, 1996, during a campaign for re-election, the 42nd U.S. President, Bill Clinton, spoke at Hillsborough High School about national education policy and "other" family issues, addressing students.

President Clinton was originally scheduled to visit during the summer sessions, but had to cancel because of hurricane warnings.

11th and 12th graders and staff were forced into the afternoon session at the new Thomas Jefferson High School at 4401 W. Cypress St until renovations of today's HHS building (built 1927–1928), were completed in 1976.

On May 3, 2008, HHS completed renovations to restore the high school to its pre-1960s luster, when it reopened its newly named gymnasium.

The five schools in the initial football league were Duval (Jacksonville), Hillsborough (Tampa), Ocala, Orlando and Summerlin Institute (Bartow).

[16] The Hillsborough Terriers football team had the oldest rivalry among Tampa Bay's high schools.

"The Barn" was known for being a hostile environment for Terrier opponents to compete in, for the HHS student body seldom stood for anything short of winning.

On May 3, 2008, a ceremony was held in Hillsborough High's newly remodeled gym to dedicate the gym, naming it; the Don Williams Athletic Center, in honor of former HHS boys basketball coach Don Williams, who led the Terriers to a 2A state championship in 1959.

Swim Coaches: Ana Cooper - 2023 - 2024 https://en.m.wikipedia.org/wiki/Jose_Alvarez_(baseball,_born_1956)Jose Alvarez- HHS Class of 74, inducted in HHS Hall of Fame 2008, HCC Baseball All State Pitcher 1976, Univ of Louisiana Lafayette 77-78 Inducted in Ragin Cajun Hall of Fame 2019, MLB Atlanta Braves 81,82,88,89, SF Giants 1990.

Helped Coach Billy Reed with the 1980 HHS Baseball team that included Dwight “Doc” Gooden, Floyd Youmans and Vance Lovelace.