1875 – School Board erects a two-story building on Wright Street. It was known as the Pensacola Academy. The Principal was Mr. John Wilmer.

1886 – New building erected on Lee Square, known as Public School No.1.

1887 –First graduating class: Albert Reed and J. Whiting Hyer.

1905 – Four year high school was organized in the old Public School No.1 building with J.B. Lockey as Principal. It becomes known as Pensacola Senior High School.

1905 – First graduating class: Dudley Barrow and Nell Richards.

1906 – The PHS yearbook is named the "Annona".

1910 – PHS was moved to what was Clubbs Junior High School, W.S. Cawthon, Principal.

1912 – B.B. Lane becomes Principal.

1916 – PHS was moved back to Public School No. 1, Ross Rogers, Principal.

1917 – Public School No. 1 burned and sessions were held again at A.V. Clubbs School.

1918 – PHS was moved to an old tabernacle building on Gregory Street, J.M. Collier, Principal.

1920 – J.H. Workman becomes Principal.

1922 – PHS was moved to the building on 614 North Palafox Street, on Lee Square.

1938 – PHS ninth grade is moved to A.V. Clubs and W.A. Blount Junior High School.

1945 – J.L. McCord becomes Principal

1948 –  Football Stadium is built. 

1953 – PHS moves to the new building at "A" and Maxwell Streets.

1957 – R.C. Lipscomb becomes Principal.

1962-63 – First black students enroll at Pensacola High School. They were Sheila Rochelle Harris and Horace Edward Harrison who graduated that year: Barbara Donaldson and Karen Robertson.

1962 – Auditorium is built.

1966 – R.C. Lipscomb, Principal, transfers to District Office as Deputy Superintendent.

1966 – Mr. John Ed Christian transferred from Tate High School to Pensacola High School as Principal, replacing Mr. Lipscomb.

1966 – L.P. McDowell, Assistant Principal, accepted position at Pensacola Junior College as Assistant Director of Maintenance.

1966 – John H. Oelerich reported as Assistant Principal replacing L.P. McDowell.

1967 – First black teacher reports to PHS: Miss Sandra Lewis.

1969 – J.P. Cone, Jr. reports as Assistant Principal.

1969 – Mr. R. E. Mabry promoted from Assistant Principal to Principal, replacing Mr. Christian who was transferred to Beggs School.

1969 – ¼ of faculty was black; many employed were transferred from Washington Jr. High School (which is now closed down) and the schools were completely integrated.

1969 –Old Pensacola High School Building on Lee Square is totaled by fire.

1974 – Ruben O. D. Askew Library is built.

1975 - R.E. Mabry retires.

1975 – J.P. Cone Jr. promoted to Principal.

1975 – Jerome E. Watson first black Assistant Principal.

1976 – Vocational Wing added.

1978 – Jerome E. Watson appointed Principal of Wedgewood Middle School.

1978 – Ella W. Sims becomes the first black woman Assistant Principal.

1979 – John H. Oelerich retired as Assistant Principal.

1979 – Jeff Moorer promoted to Assistant Principal.

1982 – Ella W. Sims resigns as Assistant Principal, transferred to District Office.

1982 – Rita E. Jones appointed as Assistant Principal.

1985 – Rita E. Jones resigns as Assistant Principal, transferred to District Office.

1985 – Hubert Williford appointed as Assistant Principal.

1986 – Hubert Williford transferred to Jim Allen Elementary School as Principal.

1986 – International Baccalaureate Diploma Program implemented.

1987 – Carl C. Johnson appointed as Assistant Principal.

1990 – Carl C. Johnson resigns as Assistant Principal, transferred to Social Studies Department as a teacher.

1990 – Sarah S. Armstrong appointed as Assistant Principal.

1990 – First International Baccalaureate Diploma Program graduating class.

1992 – Jeff L. Moorer retires.

1992 – Leo Carvalis promoted to Assistant Principal.

1994 – Mr. J. P. Cone, Jr. transferred to District Office.

1994 – Mr. Horace Jones promoted to Principal.

1997 – Mr. Horace Jones transferred to District Office.

1997 – Mr. Richard Harper appointed interim Principal.

1997 – Mr. Larry Huntley appointed Principal.

1997 – Mrs. Sarah S. Armstrong transferred to District Office.

1997 – Mr. Larry Justice appointed Assistant Principal.

1997 - Mr. Leo Carvalis transferred to District Office.

1997 – Mr. Norm Ross appointed Assistant Principal.

1999 – Mr. Larry Huntley retires.

1999 – Mr. Norm Ross appointed Principal.

1999 – Mrs. Sara Lewis appointed Assistant Principal.

2000 – West Wing added to main building.

2001 – Mr. Norm Ross promoted to Deputy Superintendent at District Office.

2001 – Mrs. Sara Lewis appointed Principal.

2001 – Mr. Lorin Lovely appointed Assistant Principal.

2001 – Mr. Larry Justice transferred to Woodham High School.

2001 – Mrs. Elaine Thomas appointed Assistant Principal.

2004 – Mr. Lorin Lovely retires.

2004 – Mr. David Williams appointed Assistant Principal.

2004 – PHS Gym destroyed by Hurricane Ivan.

2005 – PHS is ranked #8 in the country and #4 in Florida by Newsweek Magazine.

2006 – PHS ranked #38 in the country and #7 in Florida by Newsweek Magazine.

2007 – PHS ranked #36 in the country and #7 in Florida by Newsweek Magazine.

2007 – Mrs. Elaine Thomas retires.

2007 – Dr. Joy McMichael appointed Assistant Principal.

2007 – Coach Mike Bennett surpasses Coach Jim Scoggins, becoming the school's All-Time Winningest Football Coach.

2008 – PHS Gym reopens.

2008 – Mrs. Sara Lewis retires.

2008 – Mr. David Williams appointed Principal.

2008 – Mr. Thomas Rollins appointed Assistant Principal.

2008 – PHS ranked #42 in the country and #11 in Florida by Newsweek Magazine.

2009 – Jimmy Haynes Fieldhouse Opens.

2009 – PHS ranked #54 in the country and #14 in Florida by Newsweek Magazine.

2009 – PHS wins the 3A Football Championship.

2010 - PHS ranked #22 in the country and #6 in Florida by Newsweek Magazine.