| Rank | Date | Author | Size | Average | Pangram? | Title |
| 1. | Sun Oct 3, 2021 | Trenton Charlson | 21x22 | 2.45 | | NY Times, Sun, Oct 03, 2021 SNOOZEFEST |
| 2. | Sun Oct 5, 2025 | John Kugelman | 21x21 | 1.87 | | All Too Wise |
| 3. | Sun Sep 14, 2025 | Daniel Grinberg | 21x21 | 1.81 | ✅ | Bird's Eye View |
| 4. | Sun May 20, 2018 | Will Nediger | 21x21 | 1.80 | | NY Times, Sun, May 20, 2018 RHYMES, SCHMYMES |
| 5. | Sun Aug 10, 2008 | Will Nediger | 21x21 | 1.79 | ✅ | NY Times, Sun, Aug 10, 2008 INSIDE JOKES |
| 6. | Sun Nov 7, 1999 | Brendan Emmett Quigley | 21x21 | 1.78 | | NY Times, Sun, Nov 07, 1999 CUES |
| 7. | Sun Feb 7, 2021 | Katie Hale and Christina Iverson | 21x21 | 1.77 | | NY Times, Sun, Feb 07, 2021 TODDLER TALK |
| 8. | Sun Feb 16, 2020 | Sam Ezersky | 21x21 | 1.77 | ✅ | NY Times, Sun, Feb 16, 2020 NUMBER THEORY |
| 9. | Sun Apr 13, 2003 | Charles Deber | 21x21 | 1.77 | ✅ | NY Times, Sun, Apr 13, 2003 WHAT AM I? |
| 10. | Sun Jul 9, 2017 | Will Nediger | 21x21 | 1.76 | | NY Times, Sun, Jul 09, 2017 FIRST FOR KNOWLEDGE |
| 11. | Sun Jan 29, 2006 | Rich Norris | 21x21 | 1.76 | | NY Times, Sun, Jan 29, 2006 SOUNDS OF NEW ENGLAND |
| 12. | Sun Jan 27, 2008 | Mike Nothnagel | 23x23 | 1.75 | | NY Times, Sun, Jan 27, 2008 I NEED MY SPACE |
| 13. | Sun Jul 28, 2019 | Christopher Adams | 21x22 | 1.75 | | NY Times, Sun, Jul 28, 2019 ANAGRAMMAR |
| 14. | Sun Dec 8, 2019 | Emily Carroll | 21x21 | 1.75 | | NY Times, Sun, Dec 08, 2019 "LOOKIN' GOOD!" |
| 15. | Sun Aug 29, 2010 | Derek Bowman | 21x21 | 1.74 | ✅ | NY Times, Sun, Aug 29, 2010 GOING FOR A RUN |
| 16. | Sun Dec 20, 2015 | Peter Wentz | 21x21 | 1.73 | | NY Times, Sun, Dec 20, 2015 REBRANDING |
| 17. | Sun Sep 2, 2012 | Joel Fagliano | 21x21 | 1.73 | | NY Times, Sun, Sep 02, 2012 PARDON ZE INTERRUPTION |
| Sun Sep 25, 2011 | Paul Hunsberger | 21x21 | 1.73 | | NY Times, Sun, Sep 25, 2011 ENTWISTED |
| 19. | Sun Oct 9, 2011 | Brendan Emmett Quigley | 21x21 | 1.73 | ✅ | NY Times, Sun, Oct 09, 2011 GRIN AND PARROT |
| 20. | Sun Sep 1, 2019 | Finn Vigeland | 21x21 | 1.73 | | NY Times, Sun, Sep 01, 2019 THAT'S A TALL ORDER! |
| Sun Nov 29, 2009 | Will Nediger | 21x21 | 1.73 | | NY Times, Sun, Nov 29, 2009 CUED UP |
| 22. | Sun Nov 14, 2010 | Patrick Berry | 21x21 | 1.73 | | NY Times, Sun, Nov 14, 2010 DOUBLEHEADERS |
| 23. | Sun Apr 7, 2002 | Nancy Salomon | 21x21 | 1.72 | | NY Times, Sun, Apr 07, 2002 LAST ONE IN |
| 24. | Sun Jan 9, 2022 | Timothy Polin | 21x21 | 1.72 | | NY Times, Sun, Jan 09, 2022 FOOD FOR THOUGHT |
| 25. | Sun Apr 27, 2003 | Jon Delfin | 21x21 | 1.72 | ✅ | NY Times, Sun, Apr 27, 2003 TV FAVORITES |
| 26. | Sun Jan 23, 2011 | Chris A. McGlothlin | 21x21 | 1.72 | ✅ | NY Times, Sun, Jan 23, 2011 LETTER OPENERS |
| 27. | Sun Feb 8, 2009 | Alan Arbesfeld | 21x21 | 1.72 | | NY Times, Sun, Feb 08, 2009 PAJAMA PARTY |
| 28. | Sun Jun 12, 2016 | Finn Vigeland | 21x21 | 1.72 | | NY Times, Sun, Jun 12, 2016 ATTENDING PHYSICIANS |
| Sun Sep 8, 2013 | Pete Muller and Sue Keefer | 21x21 | 1.72 | | NY Times, Sun, Sep 08, 2013 BUMPER CARS |
| 30. | Sun Mar 16, 2014 | Jeremy Newton | 21x21 | 1.72 | | NY Times, Sun, Mar 16, 2014 IT'S BETTER THIS WAY |