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1 result for HEADMASTER from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Tue Jul 6, 1999	11D	Bartender?	Arthur P. Stoliar	Shortz

3 results for HEADMASTER from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Mon Sep 27, 1982	18A	Prep-school V.I.P.	Nancy McCarthy	Maleska
Sat Jun 11, 1960	26D	British principal.	Unknown	Farrar
Tue Apr 8, 1952	3D	Heely of Lawrenceville, for instance.	Unknown	Farrar

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