| Date | Grid | Clue | Author |
| Sun Jun 25, 2023 | 64D | Author who wrote "Weeds are flowers, too, once you get to know them" | John Westwig |
| Sun Oct 30, 2022 | 123A | Eeyore's creator | Addison Snell |
| Wed Aug 24, 2022 | 10D | Creator of Christopher Robin (2) | Colin Ernst |
| Mon Dec 27, 2021 | 40A | *"Winnie-the-Pooh" writer | Adam Aaronson |
| Wed May 13, 2020 | 29A | Author with a son named Christopher Robin | Benjamin Kramer |
| Sun May 3, 2020 | 36A | Creator of Christopher Robin (2) | Ben Zimmer and Brendan Emmett Quigley |
| Thu Apr 30, 2020 | 38A | "When We Were Very Young" author, 1924 | Caitlin Reid |
| Sun Dec 16, 2018 | 51D | Who wrote "Some people talk to animals. Not many listen, though. That's the problem." | Sam Ezersky |
| Sun Jan 10, 2016 | 47A | Author whose most famous character is introduced as Edward Bear | Patrick Merrell |
| Sun Apr 1, 2012 | 109A | "Now We Are Six" author (2) | Patrick Merrell |
| Sat Feb 4, 2012 | 49A | Writer about a bear | Brendan Emmett Quigley and Caleb Madison |
| Wed Nov 10, 2010 | 50A | Creator of Eeyore | Samuel A. Donaldson |
| Sun Jun 20, 2010 | 36A | Writer who wrote "A bear, however hard he tries, / Grows tubby without exercise" | Todd Gross and Ashish Vengsarkar |
| Mon Jun 7, 2010 | 42D | "Now We Are Six" poet | Lynn Lempel |
| Thu Oct 1, 2009 | 56A | "Mr. Pim Passes By" playwright | Patrick Blindauer & Rebecca Young |
| Fri Mar 6, 2009 | 27A | "The Great Broxopp" playwright, 1921 | Corey Rubin |
| Fri May 16, 2008 | 16A | His last novel was "Chloe Marr," 1946 | Kevin G. Der |
| Sat Jan 13, 2007 | 15A | Children's author who was a regular contributor to Punch | Patrick Berry |
| Wed Sep 20, 2006 | 11D | Children's author trying to dry out? | Joe DiPietro |
| Sat Jul 17, 2004 | 37D | "It's Too Late Now" autobiographer (4) | Rich Norris |
| Fri Jun 25, 2004 | 36D | He wrote "You and I have brains. The others have fluff" | Manny Nosowsky |
| Fri Jun 6, 2003 | 48A | "It's Too Late Now" autobiographer (4) | Randolph Ross |
| Fri Mar 21, 2003 | 16A | "The Red House Mystery" novelist | Myles Callum |
| Fri Sep 27, 2002 | 11D | Mr. Pim's creator | Michael Shteyman |
| Fri Jan 11, 2002 | 36A | "It's Too Late Now" autobiographer (4) | Mark Diehl |
| Sat Jun 9, 2001 | 15A | "It's Too Late Now" autobiographer (4) | Rich Norris |
| Sat Sep 23, 2000 | 33A | "Isn't it funny / How a bear likes honey?" writer | Rich Norris |
| Fri Feb 11, 2000 | 16A | Creator of a bear market? | Elizabeth C. Gorski |
| Mon Feb 1, 1999 | 31A | Winnie-the-Pooh's creator (2) | Dorothy Smitonick |
| Mon Oct 5, 1998 | 51A | Winnie-the-Pooh's creator (2) | Peter Gordon |
| Sat Jan 3, 1998 | 37D | "Toad of Toad Hall" playwright | Rich Norris |
| Fri Jul 5, 1996 | 3D | "Enchanted Places" memoir subject | M. Gaffney |
| Wed May 15, 1996 | 40A | "Now We Are Six" author (2) | A.J. Santora |
| Sat May 4, 1996 | 19D | "Bear of little brain" creator | B. Klahn |