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6 results for GRIMACE from Modern Era puzzles:

Date	Grid	Clue	Author
Sat Jan 8, 2022	13D	Reaction to a really bad pun	Freddie Cheng
Wed Mar 31, 2021	45D	Not a happy face	Trenton Charlson
Sun May 14, 2017	75D	[That's painful!]	Will Nediger
Sat May 14, 2005	38D	Possible reaction to bad news	Bob Peoples
Tue Jan 16, 1996	5D	Pained look	R. Hartman
Sat Feb 12, 1994	8A	Silent "ugh"	Rand H. Burns

1 result for GRIMACE from Variety puzzles:

Date	Type	Grid	Clue	Author
Mar 29, 2009	Acrostic	O	A kisser's contortion	Emily Cox & Henry Rathvon

7 results for GRIMACE from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sun Apr 3, 1977	87A	Make a face	Bert H. Kruse	Maleska
Sun Jul 3, 1966	4D	Facial expression.	William Lutwiniak	Farrar
Sat Mar 14, 1964	8D	Facial expression.	Unknown	Farrar
Sat Jun 26, 1954	43D	Make faces.	Diana Sessions	Farrar
Sat Apr 12, 1952	25D	Unhappy facial expression.	Unknown	Farrar
Thu Nov 9, 1950	12D	Make a face.	J. F. Kelly	Farrar
Sun Apr 11, 1943	135A	Contort the features.	Harriot T. Cooke	Farrar

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