The Book of all Headmasters in Hogwarts

Albus Dumbledore : 1956–1997 (with brief suspensions in 1993 and 1996) | House : Gryffindor
Minerva McGonagall : 1998–2010s (also served as acting head in 1993 and 1997) | House : Gryffindor
Severus Snape : 1997–1998 | House : Slytherin
Dolores Umbridge : 1996 (briefly imposed by the Ministry) | House : Slytherin
Armando Dippet : 1925–1956 | House : Unknown
Phineas Nigellus Black : Late 19th Century–1925 | House : Slytherin
Dilys Derwent : 1741–1768 | House : Unknown
Everard : Exact years unknown (Historical) | House : Unknown [1]
Elizabeth Burke : Exact years unknown | House : Slytherin (Noted as one of the few Slytherins to hold the role)
Phyllida Spore : Sometime before 1408 | House : Unknown
Edessa Sakndenberg : Sometime before 1503 | House : Unknown
Fytherley Undercliffe : Sometime before 1531 | House : Unknown
Vindictus Viridian : Sometime before 1703 | House : Unknown
Amrose Swott : Sometime before 1724 | House : Unknown
Eupraxia Mole : Sometime around 1876 | House : Unknown
Newton Scamander : Early 20th Century | House : Hufflepuff
Dexter Fortescue : Exact years unknown | House : Unknown
Basil Fronsac : Exact years unknown | House : Ravenclaw
Brian Gagwilde : Exact years unknown | House : Unknown
Walter Aragon : Exact years unknown | House : Unknown
Giffard Abbott : Exact years unknown | House : Unknown
Antonia Creaseworthy : Exact years unknown | House : Unknown
Mordicus Egg : Exact years unknown | House : Unknown
Limebert : Exact years unknown | House : Unknown
Brutus Scrimgeour : Exact years unknown | House : Unknown
Quentin Trimble : Exact years unknown | House : Unknown
Heliotrope Wilkins : Exact years unknown | House : Unknown [1]

That's all! If you have anything to add, feel free!