| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Sun, Jun 16, 2019 | 45A | Risk taker | Joel Fagliano | Shortz |
| Mon, Aug 20, 2018 | 45A | Bold type | Peter Gordon | Shortz |
| Tue, Dec 08, 2015 | 21D | Challenger | Neville Fogarty | Shortz |
| Wed, Jul 31, 2013 | 57A | Courageous one | H. David Goering | Shortz |
| Mon, Mar 05, 2012 | 15A | Challenger | Mike Nothnagel | Shortz |
| Mon, Dec 28, 2009 | 30D | Risk taker | Patrick Merrell | Shortz |
| Tue, Jan 02, 2007 | 21A | Stunt cyclist, e.g. | Sarah Keller | Shortz |
| Tue, Mar 23, 2004 | 30D | Risk taker | Fred Piscop | Shortz |
| Sun, Sep 21, 2003 | 10A | Risk taker | Randolph Ross | Shortz |
| Fri, Mar 23, 2001 | 6D | Defiant one | Elizabeth C. Gorski | Shortz |
| Sun, Aug 20, 2000 | 124A | Brave one | Charles M. Deber | Shortz |
| Sun, May 17, 1998 | 19D | Stunt man, e.g. | David J. Kahn and Hillary B. Kahn | Shortz |
| Thu, Aug 07, 1997 | 65A | Prank starter | Mark Diehl | Shortz |
| Sat, Oct 05, 1996 | 55A | Gambler | T. Payne | Shortz |
| Fri, Aug 16, 1996 | 11D | Adventurer | M. Gaffney | Shortz |
| Sun, Aug 07, 1994 | 66D | Adventurous one | Dean Niles | Shortz |