1878 - The old building of Public School 1 was erected superceding Bayview Academy.
1893 - Nathan J. Lowe was named Principal of the Tottenville District School.
1898 - Tottenville Union School was first registered as a high school by the Chancellor of the University of the State of New York.
1907 - Tottenville students spent two years at Tottenville High School and two years at Curtis High School for a high school education.
1917 - A Tottenville Intermediate School was set up, independent of Curtis High School.
1923 - Tottenville High School was made a full-fledged senior high school.
1931 - Mr. Nathan J. Lowe, Principal of Tottenville High School from its beginning, retired. Mr. William Rogers was appointed Principal.
1935 - Mr. H. Norman Ford became Acting Principal of Tottenville High School.
1936 - The building on Yetman Avenue, with a seating capacity of 1,523, was dedicated.
1937 - Dr. Mary E. Meade was appointed Principal of Tottenville High School.
1941 - A four-year vocational course was established at Tottenville High School. Mount Loretto and Lakeview Schools were made annexes of Tottenville High School.
1944 - Mrs. Mary L. Teitbohl served as Acting Principal from February 1944 to May 1944. Miss Dorothy Bonawit was appointed Principal of Tottenville High School May 1944.
1945 - The Tottenville High School Parent-Teacher Association and the Alumni Association were reactivated.
1948 - Tottenville High School celebrated its Golden Jubilee as the first accredited public high school on Staten Island.
1954 - Dr. Max Berger was installed as Principal of Tottenville High School.
1963 - Mr. David Gordon became Principal of Tottenville High School.
1965 - Mr. Paul Driscoll, former teacher and chair of the social studies department at Tottenville High School, became Principal.
1968 - After the death of Mr. Paul Driscoll, Mr. Raymond Halloran served as Interim Principal, and for the first time in its history, Tottenville High School went on extended session.
1970 - Mr. Howard Saronson was appointed Principal of Tottenville High School.
1972 - In September of 1972, Tottenville High School occupied the new building at Luten Avenue.
1974 - Tottenville High School celebrated its Diamond Jubilee as the first accredited Public High School on Staten Island.
1980 - Dr. Joseph K. Fisler, former Tottenville student, teacher, and Assistant Principal, became Tottenville High School's 10th Principal.
1984 - In May, Mr. John P. Tobin, former Assistant Principal, became Acting Principal of Tottenville High School.
1985 - In February, Mr. Herbert Balish was appointed as the 11th Principal of Tottenville.
1987 - In November, Tottenville High School was recognized as a School of Excellence by the U.S. Department of Education.
1993 - Mr. Michael Marotta was appointed Tottenville High School's Principal.
1998 - Tottenville High School celebrates its 100 year anniversary.
1999 - Mr. John P. Tuminaro was appointed as Tottenville High School's 13th Principal