Prior to 2016 the chief administrative officer of each of Yale's undergraduate residential colleges was given the honorific title Master, derived from the Latin magister and in common usage in the residential colleges of Oxford and Cambridge Universities. In 2016 the Yale Corporation voted to replace that honorific title with Head of College.

Clarence Whittlesey Mendell (1931 - 1943)

Norman Sydney Buck (1942 - 1943)

Norman Sydney Buck (1943 - 1959)  acting

Quincy Porter (1958 - 1965)

George Alfred Schrader, Jr (1959 - 1966)

John Philip Trinkaus (1966 - 1973)

Wayne Orin Southwick (1967 - 1968)  acting

William Knowlton Zinsser (1973 - 1979)

Phyllis Curtin (1979 - 1982)

John Mustard Merriman (1983 - 1990)

Worth David (1991 - 1996)

Steven B. Smith (1996 - 2011)

Elizabeth H. Bradley (2011 - 2017)

Enrique De La Cruz (2017 - Present)

The Dean serves as the chief academic officer in Yale's undergraduate residential college system.

Richard Ralph Shank (1963 - 1964)

Michael Heath Cowan (1964 - 1966)

Thomas Kennedy Edwards (1966 - 1969)

Barry Lydgate (1969 - 1973)

Lorenzo Simpson (1975 - 1976)  acting

Margarita Egan (1979 - 1983)

Marion F Freeman (1980 - 1981)  acting

Rory Browne (1983 - 1990)

Mark Schenker (1990 - 1996)

Nicole Parisier (1996 - 2003)

Thomas F. McDow (2003 - 2007)

Daniel Tauss (2007 - 2010)

Hilary Fink (2010 - 2015)

Sarah Insley (2015 - Present)