| Date | Grid | Clue | Author | Editor |
| Sat, Dec 30, 2023 | 54D | Completely black, as the sky | Simeon Seigel | Shortz |
| Sun, Nov 05, 2023 | 105D | Like a leaky pen | Rich Katz | Shortz |
| Sat, Feb 04, 2023 | 44D | Black as night | Kate Hawkins | Shortz |
| Sat, Sep 10, 2022 | 8D | Jet | Kameron Austin Collins | Shortz |
| Thu, Jan 27, 2022 | 34A | Like a stamp pad | Lewis Rothlein and Jeff Chen | Shortz |
| Thu, Aug 05, 2021 | 56A | Stained, in a way | Adam Wagner | Shortz |
| Sun, Feb 21, 2021 | 38D | Black | Matthew Stock | Shortz |
| Sat, Jan 23, 2021 | 24D | Like presses | Doug Peterson and Brad Wilber | Shortz |
| Sun, Sep 15, 2019 | 100A | Black | Andrew Kingsley | Shortz |
| Fri, Sep 22, 2017 | 20D | Extremely dark | David Steinberg | Shortz |
| Sun, Jul 02, 2017 | 110D | Black as night | Patrick Blindauer | Shortz |
| Wed, Jun 22, 2016 | 41A | Pitch-black | Fred Piscop | Shortz |
| Tue, Aug 04, 2015 | 39A | Pitch-black | Joel Fagliano | Shortz |
| Mon, Feb 16, 2015 | 8D | Jet-black | David J. Kahn | Shortz |
| Thu, Jan 10, 2013 | 47A | Black | Kevan Choset | Shortz |
| Sun, Jan 02, 2011 | 57A | One of the Pac-Man ghosts | David Levinson Wilk | Shortz |
| Thu, Dec 16, 2010 | 10A | Black | Charles Deber | Shortz |
| Tue, Sep 28, 2010 | 15A | Black | Michael Torch | Shortz |
| Sat, Jan 24, 2009 | 34A | Black as night | Mark Diehl | Shortz |
| Wed, Oct 17, 2007 | 47A | Like a starless sky | Paula Gamache | Shortz |
| Wed, Nov 17, 2004 | 64A | Jet black | Richard Silvestri | Shortz |
| Sat, Apr 10, 2004 | 48D | Pitch-black | Mark Diehl | Shortz |
| Wed, Dec 17, 2003 | 53D | Black | Leonard Williams | Shortz |
| Sun, Apr 27, 2003 | 73A | Deep black | Jon Delfin | Shortz |
| Thu, Jan 09, 2003 | 59D | Black | David J. Kahn | Shortz |
| Sun, May 14, 2000 | 95A | Black | Bill Zais and Nancy Salomon | Shortz |
| Sun, Jul 04, 1999 | 67D | Pitch-dark | Greg Staples | Shortz |
| Sun, Dec 06, 1998 | 79D | Blackened | Marjorie Richter | Shortz |
| Sun, Nov 08, 1998 | 36D | Black | Fred Piscop | Shortz |
| Fri, Dec 12, 1997 | 9D | Very dark | Manny Nosowsky | Shortz |
| Thu, Oct 09, 1997 | 44D | Black | Cathy Millhauser | Shortz |
| Thu, Sep 18, 1997 | 57D | Black and wet | Cathy Millhauser | Shortz |
| Sun, Jul 27, 1997 | 111D | Black | June Boggs | Shortz |
| Sat, May 10, 1997 | 68A | Black | Isabel Walcott | Shortz |
| Wed, Apr 02, 1997 | 16A | Like an octopus's defense | Mark Elliot Skolsky | Shortz |
| Wed, Feb 12, 1997 | 12D | Like an octopus's defense | M. E. Skolsky | Shortz |
| Thu, Nov 28, 1996 | 45A | Very dark | B. Klahn | Shortz |
| Sun, Nov 03, 1996 | 63D | Black | M. Nosowsky | Shortz |
| Mon, Feb 26, 1996 | 22A | Like printers' fingers | N. Steinberg | Shortz |