| Date | Grid | Clue | Author | Editor |
| Thu, Jan 14, 2021 | 41D | Musical role for Madonna and Patti LuPone | Aimee Lucido and Ella Dershowitz | Shortz |
| Thu, Mar 17, 2016 | 44A | 1996 Madonna starring role | David Woolf | Shortz |
| Sun, Apr 12, 2015 | 13D | First lady of the 1940s-'50s | Jeff Chen | Shortz |
| Sun, Jun 21, 2009 | 48D | "Eva is leaving" | Matt Ginsberg and Pete Muller | Shortz |
| Wed, Oct 19, 2005 | 40D | 1996 Madonna role | Levi Denham | Shortz |
| Sun, Oct 10, 2004 | 22A | Noted Madonna role | Elizabeth C. Gorski | Shortz |
| Fri, Mar 23, 2001 | 17A | Political leader who died at age 33 | Elizabeth C. Gorski | Shortz |
| Sun, May 16, 1999 | 27A | Madonna role, 1996 | Nancy Nicholson Joline | Shortz |