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7 results for GALOOT from Modern Era puzzles:

Date	Grid	Clue	Author
Wed Apr 29, 2020	41A	Big oaf	Joe DiPietro
Fri Dec 22, 2006	57A	Stumblebum	Mike Nothnagel
Sun Oct 19, 2003	13D	Lug	Nancy Nicholson Joline
Wed Oct 1, 2003	47D	Dumb ox	A. J. Santora
Sun Mar 21, 1999	59A	Palooka	Lloyd E. Pollet
Sun Jul 13, 1997	16D	Big goon	Fred Piscop
Mon Aug 22, 1994	50D	Awkward bloke	Sidney L. Robbins

8 results for GALOOT from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sun May 3, 1992	52A	Awkward guys	Rosalind Pavane	Maleska
Wed Oct 8, 1986	49D	Lummox	Shirley Soloway	Maleska
Mon Apr 24, 1978	49A	Lummox	Jordan S. Lasher	Maleska
Sun Apr 2, 1972	110A	Strange guy	Bert Kruse	Weng
Thu Nov 19, 1970	36A	Queer chap	Unknown	Weng
Sat May 23, 1964	2D	Old-time oddball.	Unknown	Farrar
Fri Sep 8, 1961	47D	Lout: Slang.	Unknown	Farrar
Wed Oct 7, 1953	22A	Awkward fellow: Slang.	Roberta Morse	Farrar

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12 ms