Headley is a surname. Notable people with the surname include:
Chase Headley (born 1984), American professional baseball playerDavid Headley (born 1960), Pakistani-American terroristDean Headley (born 1970), cricketerFrederick Webb Headley (1856–1919), English naturalistGeorge Headley (1909–1983), West Indian cricketerHeather Headley (born 1974), Trinidadian-American musicianHubert Klyne Headley (1906–1996), American composer and musicianJustina Headley (born 1968), Taiwanese-American authorRon Headley (born 1939), West Indian cricketerShari Headley (born 1964), American ActressVictor Headley (born 1959), British authorWin Headley (born 1949), American football player