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1 result for HEADWIND from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Mon Mar 6, 2023	25A	*Navigation hurdle for a sailboat	Lynn Lempel	Shortz

1 result for HEADWIND from Variety puzzles:

Date	Type	Grid	Clue	Author	Editor
Jan 3, 2010	Acrostic	F	Reason to change tacks	Emily Cox & Henry Rathvon	Shortz

2 results for HEADWIND from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Tue Apr 15, 1986	45A	Sailor's problem	Norma Steinberg	Maleska
Wed Dec 31, 1969	39D	Pilots' bane.	Unknown	Weng

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