| Date | Grid | Clue | Author | Editor |
| Wed, Mar 31, 2021 | 3D | Bemoan | Trenton Charlson | Shortz |
| Fri, Sep 29, 2017 | 52A | Greatly regret | Damon Gulczynski | Shortz |
| Sun, Jun 01, 2014 | 49D | Bemoan | Tom McCoy | Shortz |
| Mon, Oct 11, 2010 | 2D | Bemoan | Robert Fisher | Shortz |
| Tue, May 06, 2008 | 24D | "Alas, poor Yorick!," e.g. | Gary J. Whitehead | Shortz |
| Mon, Oct 08, 2007 | 22A | Bemoan | Steve Kahn | Shortz |
| Thu, Jun 07, 2007 | 55D | "Ah, for the good old days," e.g. | Nancy Salomon | Shortz |
| Fri, Apr 06, 2007 | 17A | Really regret | Will Nediger | Shortz |
| Sun, Dec 31, 2006 | 65D | Elegy | Elizabeth C. Gorski | Shortz |
| Wed, May 10, 2006 | 55A | "Guys and Dolls" song "Adelaide's ___" | Kevan Choset | Shortz |
| Fri, May 04, 2001 | 20A | Regret | Elizabeth C. Gorski | Shortz |
| Sun, Jan 09, 2000 | 30A | Weep for | Charles M. Deber | Shortz |
| Fri, Sep 17, 1999 | 26D | "Woe is me" soliloquy | Patrick D. Berry | Shortz |
| Sat, Jul 24, 1999 | 25D | Threnody | Rich Norris | Shortz |
| Sat, Feb 06, 1999 | 10D | Sing the blues | Bob Klahn and Martin Ashwood-Smith | Shortz |
| Fri, Jul 31, 1998 | 29A | Keen | John Wolting | Shortz |
| Tue, Nov 05, 1996 | 54D | Bemoan | Jeremiah Farrell | Shortz |
| Sat, Nov 04, 1995 | 44A | Jeremiad | Frank A. Longo | Shortz |