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2 results for GRAYEST from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Fri Sep 13, 2013	11D	Most dismal	Patrick Berry	Shortz
Sat Feb 18, 1995	58A	Most dreary	Stephanie Spadaccini	Shortz

4 results for GRAYEST from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sun Sep 4, 1983	65A	Most ashen	Mary Virginia Orna	Maleska
Fri Jan 23, 1976	48A	Most bleak	Sophie Fierman	Weng
Fri Apr 11, 1975	49A	Most like the old mare	Jordan S. Lasher	Weng
Sat May 1, 1971	66A	Most bleak	Unknown	Weng

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18 ms