| Rank | Date | Author | Size | Average | Pangram? | Title |
| 1. | Sun Mar 18, 2001 | Richard Silvestri | 21x21 | 1.37 | | NY Times, Sun, Mar 18, 2001 AT PRESENT |
| 2. | Sun May 13, 2007 | Jim Page | 21x21 | 1.37 | | NY Times, Sun, May 13, 2007 TWO TIMES THREE* |
| 3. | Sun Aug 2, 1998 | Nancy Nicholson Joline | 21x21 | 1.37 | | NY Times, Sun, Aug 02, 1998 "Foursomes" |
| 4. | Sun Feb 23, 1997 | Nancy Nicholson Joline | 21x21 | 1.38 | | NY Times, Sun, Feb 23, 1997 Theme: Sound Effects |
| 5. | Sun May 29, 1994 | Janet R. Bender | 21x21 | 1.39 | | NY Times, Sun, May 29, 1994 Look Both Ways |
| 6. | Sun Sep 7, 2003 | Alan Arbesfeld | 21x21 | 1.39 | | NY Times, Sun, Sep 07, 2003 INSIDE BREAK |
| 7. | Sun Jun 3, 2018 | David J. Kahn | 21x21 | 1.39 | | NY Times, Sun, Jun 03, 2018 PROVING THEM WRONG |
| 8. | Sun Aug 30, 1998 | John Wolting | 21x21 | 1.39 | | NY Times, Sun, Aug 30, 1998 "A Twist of Phrase" |
| 9. | Sun Dec 23, 2007 | Adam G. Perl | 21x21 | 1.39 | | NY Times, Sun, Dec 23, 2007 YULE OUTSOURCING |
| 10. | Sun Dec 13, 1998 | Richard Silvestri | 21x21 | 1.39 | | NY Times, Sun, Dec 13, 1998 "Sounds of the Past" |
| 11. | Sun May 4, 2014 | Mary Lou Guizzo | 21x21 | 1.40 | | NY Times, Sun, May 04, 2014 JOINED SIDES |
| 12. | Sun Jul 10, 1994 | Alvin Chase | 21x21 | 1.40 | | NY Times, Sun, July 10, 1994 Stepquote |
| 13. | Sun Nov 27, 1994 | Jacques Liwer | 21x21 | 1.40 | | NY Times, Sun, Nov 27, 1994 Per-plexities |
| 14. | Sun Jul 10, 2005 | Con Pederson | 21x21 | 1.40 | | NY Times, Sun, Jul 10, 2005 NEW AR-RANGEMENTS |
| 15. | Sun Feb 18, 2007 | David Kwong and Kevan Choset | 21x21 | 1.40 | | NY Times, Sun, Feb 18, 2007 MAGIC WORDS |
| 16. | Sun May 15, 1994 | Charles M. Deber | 21x21 | 1.40 | | NY Times, Sun, May 15, 1994 Laxicography |
| 17. | Sun Dec 3, 2006 | Patrick Merrell | 21x21 | 1.41 | | NY Times, Sun, Dec 03, 2006 PREFIX REMIX |
| 18. | Sun Feb 9, 2003 | David J. Kahn | 21x21 | 1.41 | | NY Times, Sun, Feb 09, 2003 DRAWING POWER |
| 19. | Sun Feb 12, 1995 | Alex & Victoria Black | 21x21 | 1.41 | | NY Times, Sun, Feb 12, 1995 Bureaucratically Speaking |
| 20. | Sun Aug 6, 2023 | Lisa Senzel and Jeff Chen | 21x21 | 1.41 | | What's Hanging? |
| 21. | Sun Dec 29, 2002 | Richard Silvestri | 21x21 | 1.41 | | NY Times, Sun, Dec 29, 2002 BONUS ROUNDS |
| 22. | Sun May 14, 1995 | Richard Silvestri | 21x21 | 1.42 | | NY Times, Sun, May 14, 1995 Municipal Bonds |
| 23. | Sun Oct 19, 1997 | David J. Kahn | 21x21 | 1.42 | | NY Times, Sun, Oct 19, 1997 "String Quintet" |
| 24. | Sun Nov 8, 2009 | Robert W. Harris | 21x21 | 1.42 | | NY Times, Sun, Nov 08, 2009 COLONIZATION |
| 25. | Sun Jan 25, 1998 | Dave Tuller | 21x21 | 1.42 | | NY Times, Sun, Jan 25, 1998 "Seeing Double" |
| Sun Jul 23, 1995 | Fran & Lou Sabin | 21x21 | 1.42 | | NY Times, Sun, July 23, 1995 In 1945 |
| 27. | Sun Dec 15, 2002 | RIchard Hughes | 21x21 | 1.42 | | NY Times, Sun, Dec 15, 2002 DID WHAT? |
| 28. | Sun Feb 18, 2001 | David J. Kahn | 21x21 | 1.42 | | NY Times, Sun, Feb 18, 2001 WHAT'S MY LINE? |
| 29. | Sun Jan 21, 2007 | Patrick Berry | 21x21 | 1.42 | | NY Times, Sun, Jan 21, 2007 KAREEM OF THE CROP |
| 30. | Sun Mar 25, 2007 | Fred Piscop | 21x21 | 1.42 | | NY Times, Sun, Mar 25, 2007 "OOH!" |