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1 result for WINIEST from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Sun Jul 9, 2000	91A	Most like Chianti, say	Manny Nosowsky	Shortz

1 result for WINIEST from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sun Oct 22, 1944	104D	Most bibulous.	Jack Luzzatto	Farrar

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