| Date | Grid | Clue | Author | Editor |
| Sun, Dec 06, 2020 | 59D | Hair pattern protector | Tony Orbach | Shortz |
| Tue, Jun 09, 2020 | 26A | Close-fitting headwear | Freddie Cheng | Shortz |
| Tue, Aug 27, 2019 | 1A | Head covering similar to a wave cap | Daniel Raymon | Shortz |
| Wed, Jan 17, 2018 | 14A | Close-fitting head covering | Jules Markey | Shortz |
| Mon, Oct 23, 2017 | 12D | Kerchief worn as headgear | Timothy Polin | Shortz |
| Sun, May 07, 2017 | 74D | Rapper topper | Natan Last, Finn Vigeland and the J.A.S.A. Crossword Class | Shortz |
| Fri, May 05, 2017 | 27A | Crown cover | Patrick Berry | Shortz |
| Sun, Jan 08, 2017 | 25A | Headwear the N.B.A. banned in 2005 | Peter Broda and Erik Agard | Shortz |
| Sun, Nov 27, 2016 | 105D | Hulk Hogan trademark | Matt Ginsberg | Shortz |
| Thu, Nov 03, 2016 | 32D | Rapper's headwear | Mel Rosen | Shortz |
| Fri, Jul 08, 2016 | 9D | Rapper wrapper? | Barry C. Silk | Shortz |
| Sat, Apr 25, 2015 | 26D | Headgear for Eminem | James Mulhern | Shortz |
| Mon, Sep 03, 2012 | 6D | Hip-hopper's headgear | C. W. Stewart | Shortz |
| Fri, May 21, 2010 | 47A | Hair hider | Patrick Berry | Shortz |
| Tue, May 18, 2010 | 59A | Hip-hopper's headgear | Peter A. Collins | Shortz |
| Thu, Nov 05, 2009 | 10D | Headwear banned by the N.F.L. in 2001 | Patrick Blindauer | Shortz |
| Sun, Sep 20, 2009 | 67D | Informal headwear | Michael Ashley | Shortz |
| Fri, Feb 06, 2009 | 10D | It might be worn under a cap | Frederick J. Healy | Shortz |
| Sat, Aug 04, 2007 | 20A | 50 Cent cover | Byron Walden | Shortz |
| Sun, Apr 01, 2007 | 69A | Informal head cover | Paula Gamache | Shortz |
| Wed, Mar 30, 2005 | 17A | Informal head cover | Richard Silvestri | Shortz |
| Sun, May 14, 1995 | 67D | Kerchief for protecting straightened hair | Richard Silvestri | Shortz |