KAMEHAMEHA SCHOOL FOR BOYS at Kaiwiula moving to Kapālama in 1940
| 1887-1893 | Reverend William Brewster Oleson | |
| 1893-1898 | Theodore Richards | |
| 1898-1901 | Uldrick Thompson | |
| 1901-1904 | Charles B. Dyke | |
| 1904-1914 | Perley L. Horne | |
| 1914-1915 | Ernest C. Webster | |
| 1915-1918 | Charles R. Bostwick | |
| 1918-1919 | Frank M. Watson | |
| 1919-1922 | Earl G. Bartlett | |
| 1922-1923 | Willard E. Givens | |
| 1923-1923 | J.E. Carpenter | |
| 1923-1924 | John H. Midkiff | |
| 1924-1930 | John H. Nelson | |
| 1930-1944 | Homer F. Barnes, Ph.D. | |
| 1944-1946 | Charles T. Parrent | |
| 1946-1949 | Leonard Calvert | |
| 1949-1953 | Allen A. Bailey | |
| 1953-1954 | Oscar F. Fowler | |
| 1954-1966 | Allen A. Bailey | |
| 1966-1968 | R. Burl Yarberry | |
| 1968-1969 | John E. Helfrich Ph.D. |
Merged Kamehameha Schools for Boys and Kamehameha Schools for Girls 7–12 grades (Co-ed since 1965)
| 1970-1972 | Murl W. Anderson Ph.D. | |
| 1972-1972 | Winona E. Rubin | |
| 1972-1976 | James J. Harpstrite, Ph.D. | |
| 1976-1977 | Diana Nui | |
| 1977-2005 | Anthony J. Ramos KSB 1958 |
Named Kamehameha High School in 2004
| 2005-2015 | Julian Ako KSB 1961 | |
| 2015- | Sheena Aliasa |
KAMEHAMEHA SCHOOL PREPARATORY DEPARTMENT at Kaiwiula
| 1888-1889 | Carrie A. Reamer | |
| 1889-1894 | Nancy J. Malone | |
| 1894-1909 | Alice E. Knapp | |
| 1909-1910 | Florence A. Perrott | |
| 1910-1920 | Alice E. Knapp | |
| 1920-1932 | Maude Post (closed) |
Reopening at McNeil Street and moving to Kapālama
| 1943-1960 | Lela R. Brewer | |
| 1960-1965 | Richard L. Cundy |
KAMEHAMEHA SCHOOL FOR GIRLS at Kaiwiula moving to Kapalama in 1931
| 1894-1914 | Ida May Pope | |
| 1914-1915 | Frances A. Lemmon | |
| 1915-1927 | Abbie H. Newton | |
| 1927-1942 | Maude E. Schaeffer | |
| 1942-1959 | Pauline Frederick Ph.D. | |
| 1959-1963 | Margaret L. Hotaling | |
| 1963-1970 | Gladys A. Brandt |
INTERMEDIATE DIVISION
| 1965-1982 | Diana Lord | |
| 1982-2001 | Anthony J. Ramos KSB 1958 (Principal for grades 7-12) |
MIDDLE SCHOOL (renamed)
| 2001-2007 | Sandy Young | |
| 2007- | Pua Mills Kaʻai |
ELEMENTARY DIVISION
| 1965-1982 | Marian Welz |
ELEMENTARY SCHOOL (renamed)
| 1979-1981 | Sherlyn Franklin Goo | |
| 1982-2004 | Kahale Kukea KSB 1963 | |
| 2004-2012 | Holoua Stender | |
| 2012- | Ronnie Kopp KSK 1975 |
MAUI CAMPUS AT PUKALANI (opened in 1996)
| 1996-2001 | K-8 | Mrs. Cordy MacLaughlin | ||
| 2001-2002 | K-8 | Mrs. Lee Ann DeLima, interim | ||
| 2002-2003 | K-8 | Mrs. Lee Ann DeLima | ||
| 2002-2003 | (9-12) | Mr. Mitchell Kalauli | ||
| 2003-2014 | K-5 | Dr. Paul Prevenas | ||
| 2003-2006 | 6-8 | Mrs. Lee Ann DeLima | ||
| 2004-2004 | 9-12 | Mrs. Lee Ann DeLima, interim | ||
| 2004-2010 | 9-12 | Dr. Warren Heitz, Jr. | ||
| 2007- | 6-8 | Mrs. Lois Nishikawa | ||
| 2010-2012 | 9-10 | Mr. Lance Cagasan, interim | ||
| 2010-2012 | 11-12 | Ms. Jay-R Kaawa, interim | ||
| 2012- | 9-10 | Mr. Lance Cagasan | ||
| 2012- | 11-12 | Ms. Jay-R Kaawa |
HAWAIʻI CAMPUS AT KEAʻAU (opened in 1996)
| 1996 | K-3 | Barbara Robertson | ||
| 1976 | K-4 | Barbara Robertson | ||
| 1998 | K-5 | Barbara Robertson | ||
| 1999 | K-6 | Barbara Robertson, principal | ||
| Eva Bogue, vice-principal | ||||
| 2000 | K-7 | Barbara Roberton, principal | ||
| Eva Bogue, vice-principal | ||||
| 2001-2002 | K-8 | Barbara Robertson, principal | ||
| Eva Bogue, vice-principal | ||||
| 2003 | K-8 | Barbar Robertson, principal | ||
| Eva Bogue, vice-principal | ||||
| 9 | Ninia Aldrich, high school principal | |||
| 2004 | K-8 | Barbara Robertson, principal | ||
| Eva Bogue, vice-principal | ||||
| 9, 10 | Ninia Aldrich, high school principal | |||
| 2005 | K-8 | Barbara Robertson, principal | ||
| Eva Bogue, vice-principal | ||||
| 9, 10, 11 | Ninia Aldrich, high school principal | |||
| Phil Aganus, high school VP | ||||
| 2006-2008 | K-5 | Kāhealani Nae`ole-Wong | ||
| 6-8 | John Colson | |||
| 9-12 | Ninia Aldrich, high school principal | |||
| Phil Aganus, high school VP | ||||
| 2009-2011 | K-5 | Kāhealani Nae`ole-Wong | ||
| 6-8 | Scott De Sa | |||
| 9-12 | Ninia Aldrich, high school principal | |||
| Phil Aganus, high school VP | ||||
| 2012 | K-5 | Kāhealani Nae`ole-Wong | ||
| 6-8 | Scott De Sa | |||
| Jay Chow, VP | ||||
| 9-12 | Phil Aganus, acting HS principal | |||
| Lorelei “Pua Perreira, HS acting VP | ||||
| 2013 | K-5 | Kāhealani Nae`ole-Wong | ||
| 6-8 | Scott De Sa | |||
| Jay Chow, VP | ||||
| 9-12 | Lehua Veincent, high school principal | |||
| Phil Aganus, high school VP |
Kamehameha Schools’ policy is to give preference to applicants of Hawaiian ancestry to the extent permitted by law.
