| Date | Grid | Clue | Author | Editor |
| Fri Sep 3, 2021 | 9D | Actor John of Broadway's "Carousel" | Brendan Emmett Quigley and Paolo Pasco | Shortz |
| Sun Aug 8, 2021 | 66A | Bonnie with five Top 40 hits in the 1990s | Christina Iverson and Jeff Chen | Shortz |
| Fri Nov 23, 2018 | 7D | Bonnie with five 1990s Top 40 hits | Temple Brown | Shortz |
| Mon Feb 26, 2018 | 2D | Bonnie who sang "I Can't Make You Love Me" | Andrea Carla Michaels and Mark Diehl | Shortz |
| Sun Jul 23, 2017 | 64D | Singer Bonnie (10) | Caleb Madison | Shortz |
| Wed Mar 30, 2016 | 32D | "Nick of Time" singer Bonnie | Andrew Reynolds | Shortz |
| Sun Mar 20, 2016 | 61D | "Something to Talk About" singer, 1991 (4) | Joel Fagliano | Shortz |
| Sun Oct 4, 2015 | 5A | Bonnie who sang "Nick of Time" (2) | Jeremy Newton | Shortz |
| Sun Nov 16, 2014 | 15D | Bonnie who sang "Nick of Time" (2) | Andrew J. Ries | Shortz |
| Fri Nov 1, 2013 | 41A | "Something to Talk About" singer, 1991 (4) | Brad Wilber | Shortz |
| Fri Nov 18, 2011 | 30D | "Love Sneakin' Up on You" singer, 1994 | Joe DiPietro | Shortz |
| Sat Oct 22, 2011 | 6D | Activist/singer Bonnie | Patrick Berry | Shortz |
| Thu Aug 25, 2011 | 49A | John who starred in Broadway's original "Carousel" | Patrick Blindauer & Francis Heaney | Shortz |
| Fri Aug 6, 2010 | 48A | She won three Grammys for her 1989 album "Nick of Time" | Patrick Berry | Shortz |
| Tue Mar 30, 2010 | 18A | Singer Bonnie (10) | Elizabeth C. Gorski | Shortz |
| Fri Dec 4, 2009 | 21D | Singer with the 5x platinum album "Nick of Time," 1989 | Martin Ashwood-Smith | Shortz |
| Sun Oct 11, 2009 | 61D | Grammy winner Bonnie (2) | Randolph Ross | Shortz |
| Tue Sep 15, 2009 | 28D | Singer Bonnie (10) | Fran and Lou Sabin | Shortz |
| Sun Jul 12, 2009 | 53D | Bonnie in the Rock and Roll Hall of Fame | Alan Arbesfeld | Shortz |
| Sat Apr 11, 2009 | 44A | "Something to Talk About" Grammy winner, 1991 | Karen M. Tracey | Shortz |
| Fri Feb 27, 2009 | 40A | "Something to Talk About" singer, 1991 (4) | Joe DiPietro | Shortz |
| Thu Sep 25, 2008 | 43D | John ___, Doris Day's co-star in "The Pajama Game" | Victor Fleming | Shortz |
| Sun Oct 8, 2006 | 8D | John of Broadway's "Carousel" | Fred Piscop | Shortz |
| Thu Sep 21, 2006 | 25D | "Something to Talk About" singer, 1991 (4) | Stella Daily and Bruce Venzke | Shortz |
| Mon Mar 1, 2004 | 31D | Singer Bonnie (10) | Gail Grabowski | Shortz |
| Fri Jan 23, 2004 | 9D | Day's "The Pajama Game" co-star | Sherry O. Blackard | Shortz |
| Fri Aug 15, 2003 | 13D | "Something to Talk About" singer | Jim Page | Shortz |
| Thu Nov 28, 2002 | 49D | 1989 Grammy winner for "Nick of Time" (2) | Patrick Merrell | Shortz |
| Thu Oct 31, 2002 | 8D | Singer Bonnie (10) | Dave and Diane Epperson | Shortz |
| Fri Jan 11, 2002 | 26A | 1989 Grammy winner for "Nick of Time" (2) | Mark Diehl | Shortz |
| Sun Dec 30, 2001 | 48A | "Luck of the Draw" singer | Elizabeth C. Gorski | Shortz |
| Sun Aug 5, 2001 | 30D | Singer Bonnie (10) | Peter Gordon | Shortz |
| Mon Jun 4, 2001 | 59A | Singer Bonnie (10) | Patrick Jordan | Shortz |
| Sun Feb 25, 2001 | 99A | Singer Bonnie (10) | Greg Staples | Shortz |
| Wed Mar 1, 2000 | 6D | Grammy winner Bonnie (2) | M. Francis Vuolo | Shortz |
| Wed Mar 18, 1998 | 57D | Singer Bonnie (10) | Susan Smith | Shortz |
| Sun Dec 22, 1996 | 14D | "Nick of Time" Grammy winner | F. Hansen | Shortz |
| Mon Jun 12, 1995 | 38A | Singer Bonnie (10) | Robert Zimmerman | Shortz |