| Date | Grid | Clue | Author | Editor |
| Mon Mar 11, 2024 | 52A | Tic-tac-toe win (13) | Rebecca Goldstein and Rachel Fabi | Shortz |
| Sun Feb 18, 2024 | 99D | "I'm not working right now," in email shorthand | Sid Sivakumar | Shortz |
| Mon Jan 29, 2024 | 39D | Winning tic-tac-toe line | Garrett Chalfin and Andrew Kingsley | Shortz |
| Tue Oct 3, 2023 | 65D | Away from work, for short | Troy Laedtke | Shortz |
| Wed Sep 27, 2023 | 2D | On vacation, in work calendar shorthand | Scott Koenig | Shortz |
| Sat Jun 17, 2023 | 35A | Off from work, in emails | Ryan McCarty | Shortz |
| Tue Jan 10, 2023 | 31A | Winning tic-tac-toe line, when player X isn't paying attention | Emily Rourke | Shortz |
| Sun Mar 6, 2022 | 10D | Worker's "on vacation" inits. | Matthew Stock and Will Nediger | Shortz |
| Thu Jan 20, 2022 | 43A | Rare tic-tac-toe win | Howard Barkin | Shortz |
| Wed Nov 17, 2021 | 29A | Hugs, on a love letter | Anne Grae Martin | Shortz |
| Mon Dec 21, 2020 | 23A | Tic-tac-toe win (13) | Sarah Keller and Derek Bowman | Shortz |
| Sun Sep 8, 2019 | 58A | Hugs, in a letter (2) | Joe DiPietro | Shortz |
| Tue Apr 23, 2019 | 32D | Tic-tac-toe win (13) | Amanda Chung and Karl Ni | Shortz |
| Sun Jan 21, 2018 | 58D | "Hollywood Squares" win (2) | Victor Barocas and Andy Kravis | Shortz |
| Sun Dec 17, 2017 | 105D | Win on "Hollywood Squares" | Andrew J. Ries | Shortz |
| Sat Jul 29, 2017 | 26A | Setting after resetting | Erik Agard | Shortz |
| Sun Sep 4, 2016 | 110D | Game-winning line | Tom McCoy | Shortz |
| Sun Aug 21, 2016 | 28D | It's as good as XXX | Kathy Matheson and Jeff Chen | Shortz |
| Tue Jul 28, 2015 | 59A | Tic-tac-toe winner (8) | Caleb Emmons | Shortz |
| Sun Jul 19, 2015 | 114D | Game-winning row | Tom McCoy | Shortz |
| Mon Jan 26, 2015 | 30D | Winning "Hollywood Squares" line | Ian Livengood | Shortz |
| Tue Jan 6, 2015 | 16A | Winning tic-tac-toe row (3) | Joel Fagliano | Shortz |
| Mon Sep 8, 2014 | 35D | Tic-tac-toe winner (8) | Dan Schoenholz | Shortz |
| Sat Jul 26, 2014 | 45A | Queenside castle indicator, in chess | Julian Lim | Shortz |
| Sun Oct 27, 2013 | 86A | Tic-tac-toe winner (8) | Brendan Emmett Quigley | Shortz |
| Sun Aug 26, 2012 | 113D | Hugs, in a love letter | Amanda Yesnowitz and Doug Peterson | Shortz |
| Sun Apr 8, 2012 | 125D | Tic-tac-toe winner (8) | Daniel A. Finan | Shortz |
| Thu Oct 27, 2011 | 33A | Spooky sound | Kurt Mueller | Shortz |
| Mon Aug 15, 2011 | 13D | Tic-tac-toe victory | Stan Newman | Shortz |
| Wed Jun 1, 2011 | 32D | Tic-tac-toe line ... and a hint to this puzzle's theme | Elizabeth C. Gorski | Shortz |
| Thu Dec 23, 2010 | 33D | Tic-tac-toe win (13) | Oliver Hill and Eliza Bagg | Shortz |
| Sat Jul 17, 2010 | 16A | Winning lineup | Mark Diehl | Shortz |
| Mon Oct 13, 2008 | 21A | Tic-tac-toe win (13) | Anthony J. Salvia | Shortz |
| Sun Nov 4, 2007 | 51A | "Hollywood Squares" line | Bob Klahn | Shortz |
| Wed Oct 17, 2007 | 23A | Noughts-and-crosses win | Paula Gamache | Shortz |
| Sun Sep 2, 2007 | 58D | Win in a children's game | Lee Glickstein and Nancy Salomon | Shortz |
| Sat Jun 30, 2007 | 34D | Line struck through by a winner | Byron Walden | Shortz |
| Sun Apr 15, 2007 | 115D | Resetting setting (2) | Brendan Emmett Quigley | Shortz |
| Sun Feb 11, 2007 | 90D | Tic-tac-toe win (13) | Mark Feldman | Shortz |
| Mon Aug 21, 2006 | 39D | Tic-tac-toe win (13) | Elayne Cantor | Shortz |
| Fri Jun 2, 2006 | 51A | Resetting setting (2) | Jim Page | Shortz |
| Mon Oct 31, 2005 | 49A | Winning tic-tac-toe row (3) | Jim Hyres | Shortz |
| Thu Aug 11, 2005 | 17A | New pedometer reading (3) | Michael Shteyman | Shortz |
| Thu Aug 11, 2005 | 57A | Hugs, symbolically (3) | Michael Shteyman | Shortz |
| Thu Aug 11, 2005 | 30D | Tic-tac-toe winner (8) | Michael Shteyman | Shortz |
| Thu Aug 11, 2005 | 32D | Queenside castle, in chess notation (3) | Michael Shteyman | Shortz |
| Wed Mar 16, 2005 | 34A | Hugs, in a letter (2) | Holden Baker | Shortz |
| Sun Jan 2, 2005 | 115D | Tic-tac-toe winner (8) | Patrick Merrell | Shortz |
| Sun Jul 4, 2004 | 89A | Noughts in noughts-and-crosses | Elizabeth C. Gorski | Shortz |
| Tue Mar 16, 2004 | 24A | Tic-tac-toe winner (8) | Ron Sweet | Shortz |
| Mon Jan 5, 2004 | 36A | Tic-tac-toe win (13) | Allan E. Parrish | Shortz |
| Sat Nov 22, 2003 | 20A | Game winner | Robert H. Wolfe | Shortz |
| Sun Aug 31, 2003 | 118D | Hugs, symbolically (3) | Fred Piscop | Shortz |
| Wed Aug 27, 2003 | 17A | XXX counterpart | Manny Nosowsky | Shortz |
| Sun Dec 8, 2002 | 68D | Queenside castle, in chess notation (3) | Peter Gordon | Shortz |
| Sun Nov 24, 2002 | 8D | "Hollywood Squares" win (2) | Nancy Salomon and Lee Glickstein | Shortz |
| Sun Oct 13, 2002 | 64D | Tic-tac-toe win (13) | Elizabeth C. Gorski | Shortz |
| Sun Oct 13, 2002 | 66D | New pedometer reading (3) | Elizabeth C. Gorski | Shortz |
| Sat Feb 9, 2002 | 24A | Winning sequence | Rich Norris | Shortz |
| Sun Dec 30, 2001 | 102A | New pedometer reading (3) | Elizabeth C. Gorski | Shortz |
| Tue Jun 26, 2001 | 63D | A winning combination in today's puzzle theme | Stephen Windheim | Shortz |
| Wed Jun 20, 2001 | 51A | Queenside castle, in chess notation (3) | Jay Sullivan | Shortz |
| Thu May 31, 2001 | 59A | Hockey shutout | Robert H. Wolfe | Shortz |
| Wed May 23, 2001 | 42D | Scoreboard line under RHE, maybe | Alan Arbesfeld | Shortz |
| Mon Sep 25, 2000 | 21A | Winning tic-tac-toe row (3) | Peter Gordon | Shortz |
| Wed Jul 1, 1998 | 46A | Tic-tac-toe win (13) | Fred Piscop | Shortz |
| Thu Feb 13, 1997 | 21A | Hugs, symbolically (3) | F. Longo | Shortz |
| Mon Nov 11, 1996 | 42A | Tic-tac-toe win (13) | S. Spadaccini | Shortz |
| Mon Jul 29, 1996 | 61D | Tic-tac-toe win (13) | F. Piscop | Shortz |
| Mon Jul 1, 1996 | 60D | Tic-tac-toe win (13) | S. Spadaccini | Shortz |
| Thu Mar 7, 1996 | 43A | Tic-tac-toe row | C. Millhauser | Shortz |
| Sat Sep 2, 1995 | 34A | Tic-tac-toe winner (8) | Manny Nosowsky | Shortz |
| Wed May 24, 1995 | 15A | Tripmeter setting | Wayne Robert Williams | Shortz |
| Fri Oct 7, 1994 | 42D | Tic-tac-toe triumph | Bryant White | Shortz |