| Date | Grid | Clue | Author | Editor |
| Sun, Apr 18, 2021 | 106A | Writer Horatio | Johan Vass | Shortz |
| Sat, Oct 31, 2020 | 23A | Hiss at a Congressional hearing | Stella Zawistowski | Shortz |
| Tue, May 14, 2019 | 17A | "Tattered Tom" author Horatio | Damon Gulczynski | Shortz |
| Sun, Aug 14, 2016 | 6D | Rags-to-riches writer | Ian Livengood | Shortz |
| Sun, Apr 12, 2015 | 64D | Horatio who wrote the Tattered Tom series | Jeff Chen | Shortz |
| Wed, Sep 15, 2010 | 19A | Horatio who wrote about down-and-out boys | Zoe Wheeler, Brown University '12 | Shortz |
| Sun, Feb 28, 2010 | 68D | Rags-to-riches author Horatio | Yaakov Bendavid | Shortz |
| Sun, Apr 05, 2009 | 38A | Writer Horatio | Charles Deber | Shortz |
| Sat, Aug 09, 2008 | 38A | "Luck and Pluck" author | Mark Diehl | Shortz |
| Sun, Jun 01, 2008 | 43D | "Tattered Tom" author | Patrick Berry | Shortz |
| Sun, May 04, 2008 | 15D | "Sink or Swim" author | Richard Silvestri | Shortz |
| Mon, Mar 05, 2007 | 50D | "Ragged Dick" writer Horatio | Fred Piscop | Shortz |
| Thu, Jan 11, 2007 | 41A | Author of "Jed, the Poor House Boy" | Lee Glickstein and Nancy Salomon | Shortz |
| Sun, Jan 01, 2006 | 85A | Tattered Tom's creator | Joe DiPietro | Shortz |
| Sun, Nov 06, 2005 | 105D | "Risen From the Ranks" writer | Elizabeth C. Gorski | Shortz |
| Wed, Nov 02, 2005 | 27D | Tattered Tom's creator | Randall J. Hartman | Shortz |
| Tue, Sep 23, 2003 | 67A | "Ragged Dick" author | Nancy Salomon and Gail Grabowski | Shortz |
| Mon, Jun 16, 2003 | 53D | Author Horatio | Norma Johnson | Shortz |
| Sun, Oct 13, 2002 | 19D | Tattered Tom's creator | Elizabeth C. Gorski | Shortz |
| Wed, Aug 07, 2002 | 3D | Ragged Dick creator | Randolph Ross | Shortz |
| Thu, Jan 10, 2002 | 30A | Tattered Tom's creator | Alex Vaughn | Shortz |
| Tue, Nov 27, 2001 | 12D | "Ragged Dick" author | Ed Early | Shortz |
| Thu, Dec 21, 2000 | 56D | Popular early serials writer | Manny Nosowsky | Shortz |
| Fri, Sep 18, 1998 | 48D | Ragged Dick's creator | Frank Longo | Shortz |
| Sun, Mar 08, 1998 | 64D | Tattered Tom's creator | Richard Silvestri | Shortz |
| Thu, Feb 05, 1998 | 33A | Hiss in history | Cathy Millhauser | Shortz |
| Mon, Aug 25, 1997 | 30D | Creator of the Ragged Dick books | Randall J. Hartman | Shortz |
| Tue, Dec 19, 1995 | 50A | Writer of boys' tales | Marie Heller | Shortz |
| Fri, Nov 10, 1995 | 60A | Innocent Hiss? | Bryant White | Shortz |
| Sun, Sep 17, 1995 | 54D | "Luck and Pluck" writer | Stanley Newman | Shortz |
| Tue, Sep 12, 1995 | 45A | "Ragged Dick" author | Gregory E. Paul | Shortz |
| Sun, Mar 12, 1995 | 125A | "Ragged Dick" writer | Charles M. Deber | Shortz |
| Tue, Jun 07, 1994 | 19A | Rags-to-riches writer | Ernie Furtado | Shortz |
| Mon, Apr 04, 1994 | 59A | Rags-to-riches writer | Betty Jorgensen | Shortz |
| Thu, Jan 27, 1994 | 50A | "Luck and Pluck" writer | Betty Jorgensen | Shortz |