| Date | Grid | Clue | Author |
| Tue Feb 7, 2023 | 62D | Author/illustrator Silverstein (3) | Ellen Leuschner |
| Wed Feb 9, 2022 | 54D | Author Silverstein (15) | Grant Thackray |
| Sat Sep 25, 2021 | 25D | Poet Silverstein (2) | Adam Simon Levine |
| Mon Nov 30, 2020 | 23A | Writer/illustrator Silverstein (5) | Emma Craven-Matthews |
| Sun Oct 18, 2020 | 110D | Children's poet Silverstein | Miriam Estrin |
| Mon Apr 6, 2020 | 15D | Silverstein who wrote and illustrated "The Giving Tree" (2) | Andrea Carla Michaels and Brian Thomas |
| Thu May 9, 2019 | 19A | Children's author Silverstein (3) | Lewis Rothlein |
| Fri Jan 25, 2019 | 47A | Writer/illustrator Silverstein (5) | Zhouqin Burnikel |
| Mon Feb 19, 2018 | 45A | Author Silverstein (15) | Bruce Haight |
| Sun Dec 10, 2017 | 6A | Cartoonist Silverstein (5) | Erik Agard and Laura Braunstein |
| Sat Oct 21, 2017 | 5D | First name in children's literature | Samuel A. Donaldson and Brad Wilber |
| Mon Jul 10, 2017 | 14D | Poet/illustrator Silverstein (2) | Timothy Polin |
| Wed May 31, 2017 | 8D | Poet Silverstein (2) | Jacob Stulberg |
| Wed Aug 31, 2016 | 35D | Silverstein who wrote "A Boy Named Sue" (3) | Ned White |
| Wed Mar 9, 2016 | 47A | Author Silverstein (15) | John Guzzetta |
| Sun Jan 10, 2016 | 12A | Silverstein who wrote "A Boy Named Sue" (3) | Patrick Merrell |
| Thu Aug 20, 2015 | 60D | Silverstein who wrote "A Boy Named Sue" (3) | Jules P. Markey |
| Thu Aug 28, 2014 | 7D | Writer/illustrator Silverstein (5) | Ned White |
| Tue Feb 18, 2014 | 59D | Children's author Silverstein (3) | David Steinberg |
| Sun Mar 31, 2013 | 32A | Children's author Silverstein (3) | Caleb Madison |
| Thu Nov 29, 2012 | 5D | Silverstein of kid-lit | Sharon Delorme |
| Sat Dec 17, 2011 | 31D | Author Silverstein (15) | Tom Heilman |
| Sat Nov 12, 2011 | 51A | Record producer Talmy | Barry C. Silk |
| Thu Oct 7, 2010 | 22A | Silverstein who wrote "The Giving Tree" | Patrick Blindauer |
| Wed Jul 21, 2010 | 37D | Poet/illustrator Silverstein (2) | Oliver Hill |
| Thu May 27, 2010 | 33A | "The Giving Tree" author Silverstein | Josh Knapp |
| Tue Mar 2, 2010 | 27A | Author Silverstein (15) | Elizabeth C. Gorski |
| Wed Dec 9, 2009 | 43A | Author Silverstein (15) | Peter A. Collins |
| Tue Sep 29, 2009 | 26A | Silverstein of children's literature | Paula Gamache |
| Mon Sep 21, 2009 | 42A | Writer/illustrator Silverstein (5) | Mark Feldman |
| Wed Jul 2, 2008 | 3D | "Where the Sidewalk Ends" author Silverstein | Daniel Kantor |
| Thu Jun 19, 2008 | 5D | Silverstein who wrote and illustrated "The Giving Tree" (2) | Joe Krozel |
| Sun Apr 27, 2008 | 4D | Writer/illustrator Silverstein (5) | Oliver Hill |
| Sun Oct 28, 2007 | 94D | Illustrator Silverstein (6) | Ben Tausig |
| Fri Jul 13, 2007 | 55D | Author Silverstein (15) | Manny Nosowsky |
| Thu Apr 19, 2007 | 6A | Writer Silverstein (3) | Henry Hook |
| Fri Feb 23, 2007 | 46A | Poet/cartoonist Silverstein | Patrick Merrell |
| Sun Feb 4, 2007 | 49A | Author Silverstein (15) | Paul Guttormsson |
| Thu Dec 14, 2006 | 64A | Author Silverstein (15) | Ed Early |
| Fri Jun 23, 2006 | 20A | His kids' book "Falling Up" is dedicated to his son Matt | Bruce Venzke and Stella Daily |
| Thu Mar 23, 2006 | 50D | Author Silverstein (15) | Ethan Cooper |
| Tue Mar 14, 2006 | 5A | Author/illustrator Silverstein (3) | Lynn Lempel |
| Fri Sep 23, 2005 | 50D | Rock producer Talmy | Levi Denham |
| Tue Sep 13, 2005 | 17A | Author Silverstein (15) | Stella Daily and Bruce Venzke |
| Sat Sep 25, 2004 | 47D | Author Silverstein (15) | Byron Walden |
| Sun Mar 28, 2004 | 38D | Illustrator Silverstein (6) | David J. Kahn |
| Sun Aug 10, 2003 | 33A | Author/illustrator Silverstein (3) | Cathy Millhauser |
| Tue Jun 17, 2003 | 39D | Author Silverstein (15) | Susan Harrington Smith |
| Wed Apr 24, 2002 | 34D | Author Silverstein (15) | Sheldon Benardo |
| Wed Oct 25, 2000 | 13D | Cartoonist Silverstein (5) | Nick Grivas |
| Wed Mar 15, 2000 | 7D | Cartoonist Silverstein (5) | Jim Page |
| Thu Mar 4, 1999 | 27D | Illustrator Silverstein (6) | Cathy Millhauser |
| Sun Nov 29, 1998 | 15A | Illustrator Silverstein (6) | Matt Gaffney |
| Fri Jun 26, 1998 | 19A | Author Silverstein (15) | Frank Longo |
| Sun Jun 14, 1998 | 51D | Illustrator Silverstein (6) | Manny Nosowsky |
| Thu Nov 7, 1996 | 47A | Writer Silverstein (3) | G. R. Ferguson |
| Fri Apr 12, 1996 | 14D | Illustrator Silverstein (6) | M. Nosowsky |
| Thu Apr 4, 1996 | 53D | Satirist Silverstein (2) | M. Diehl |
| Sun Mar 3, 1996 | 32D | Satirist Silverstein (2) | B. Klahn |
| Tue Aug 1, 1995 | 59D | Writer Silverstein (3) | Jonathan Schmatzbach |
| Wed Jan 18, 1995 | 40D | Cartoonist Silverstein (5) | Wayne Robert Williams |
| Sun Jul 3, 1994 | 89D | Artist / author Silverstein | A.J. Santora |
| Fri May 27, 1994 | 39D | Cartoonist Silverstein (5) | Chet Currier |