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There are 16 words beginning with HEADM

HEADMAN	• headman n. Alternative form of head man. • headman n. (Informal, rare, chiefly India) headmaster. • head␣man n. The person in charge of an organization, clan, tribe, or other group.
HEADMEN	• headmen n. Plural of headman. • head␣men n. Plural of head man. • HEADMAN n. a foreman.
HEADMARK	• headmark n. The distinction or peculiarity of the head, face, or features used in distinguishing each individual… • headmark n. A headland marking the limit of a field. • headmark n. A credit (as toward a prize to be awarded) given to a pupil for reaching the head position in an examination…
HEADMOST	• headmost adj. Closest to the front of a group or pack. • HEADMOST adj. with head first.
HEADMARKS	• headmarks n. Plural of headmark. • HEADMARK n. a peculiar characteristic.
HEADMASTER	• headmaster n. (Chiefly UK) A male school principal. • HEADMASTER n. a man heading the staff of a school.
HEADMASTERS	• headmasters n. Plural of headmaster. • HEADMASTER n. a man heading the staff of a school.
HEADMASTERLY	• headmasterly adj. In a manner befitting a headmaster. • HEADMASTERLY adj. like a headmaster.
HEADMISTRESS	• headmistress n. (Chiefly Britain) A female school principal. • HEADMISTRESS n. a woman heading the staff of a private school.
HEADMISTRESSY	• headmistressy adj. Resembling or characteristic of a headmistress. • HEADMISTRESSY adj. like a headmistress, bossy.
HEADMASTERLIER	• HEADMASTERLY adj. like a headmaster.
HEADMASTERSHIP	• headmastership n. The role or position of headmaster. • HEADMASTERSHIP n. the office of headmaster.
HEADMISTRESSES	• headmistresses n. Plural of headmistress. • HEADMISTRESS n. a woman heading the staff of a private school.
HEADMASTERLIEST	• HEADMASTERLY adj. like a headmaster.
HEADMASTERSHIPS	• headmasterships n. Plural of headmastership. • HEADMASTERSHIP n. the office of headmaster.
HEADMISTRESSIER	• HEADMISTRESSY adj. like a headmistress, bossy.

Scrabble words — in black are valid world wide — in RED are not valid in North America — in GREEN are valid only in North America.
Definitions are short excerpt from the WikWik.org and 1Word.ws.

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English Wiktionary: 32 words
Scrabble in French: no word
Scrabble in Spanish: no word
Scrabble in Italian: no word
Scrabble in German: no word
Scrabble in Romanian: no word

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