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1 result for WEARIEST from Modern Era puzzles:

Date	Grid	Clue	Author
Thu Aug 10, 2017	18D	Spent the most?	John E. Bennett and Jeff Chen

7 results for WEARIEST from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sun Sep 19, 1976	58A	Most spent	Eugene T. Maleska	Weng
Mon Aug 4, 1969	26A	Most bushed.	Unknown	Weng
Wed Sep 4, 1968	20A	Most exhausted.	Unknown	Farrar
Tue Feb 8, 1966	45A	Most tiresome.	Unknown	Farrar
Sat May 25, 1963	46A	Most jaded.	Unknown	Farrar
Fri Nov 8, 1957	33A	Most exhausted.	Unknown	Farrar
Wed Nov 19, 1952	37D	Most exhausted.	Unknown	Farrar

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