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2 results for HEEDLESS from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Sat Aug 3, 2002	52A	Foolhardy	Patrick Berry	Shortz
Fri Apr 9, 1999	20A	Incautious	Manny Nosowsky	Shortz

9 results for HEEDLESS from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Fri Sep 27, 1991	40A	Unmindful	Norma Steinberg	Maleska
Sat Oct 8, 1977	21D	"How many mischiefs should ensue his ___ haste": Spenser	Jack Luzzatto	Maleska
Sun Jun 18, 1972	103D	Rash	Herbert Ettenson	Weng
Wed Nov 12, 1969	42A	Unobservant.	Unknown	Weng
Sun Jun 9, 1968	93D	Inattentive.	S. Lambert	Farrar
Thu May 14, 1964	45A	Unmindful.	Unknown	Farrar
Thu Dec 22, 1960	20A	Indifferent.	Unknown	Farrar
Fri Jul 12, 1957	9D	Unmindful.	A. H. Drummond Jr.	Farrar
Tue Jun 25, 1957	32A	Inattentive.	Thomas Meekin	Farrar

Anagram:

18 ms