| Date | Grid | Clue | Author | Editor |
| Tue, Sep 27, 2022 | 1A | "Go directly to ___" (order in Monopoly) | Peter Koetters | Shortz |
| Mon, Jun 21, 2021 | 57A | Martin Luther King's "Letter From Birmingham ___" | Jacob Stulberg | Shortz |
| Sun, Mar 28, 2021 | 21D | Corner space in Monopoly | Olivia Mitra Framke | Shortz |
| Mon, Jul 13, 2020 | 52D | One corner on a Monopoly board | Erik Agard | Shortz |
| Wed, Jan 03, 2018 | 1D | Pokey | Bruce Haight | Shortz |
| Tue, Nov 07, 2017 | 4D | Corner square in Monopoly | Greg Poulos | Shortz |
| Mon, May 01, 2017 | 1D | Monopoly space with the words "Just Visiting" | Ed Sessa | Shortz |
| Sun, Jan 10, 2016 | 103D | One corner of a Monopoly board | Patrick Merrell | Shortz |
| Wed, Oct 07, 2015 | 12D | One corner of a Monopoly board | Julian Lim | Shortz |
| Mon, Feb 16, 2015 | 49D | Monopoly space that says "Just Visiting" | David J. Kahn | Shortz |
| Sun, Oct 26, 2014 | 76D | Lock up | Caleb Emmons | Shortz |
| Tue, Feb 11, 2014 | 31A | Monopoly square between Connecticut Avenue and St. Charles Place | Matthew E. Paronto and Jeff Chen | Shortz |
| Wed, Jan 09, 2013 | 49A | Corner Monopoly square | David Ben-Merre | Shortz |
| Mon, Oct 01, 2012 | 8D | First corner after "Go" in Monopoly | Susan Gelfand | Shortz |
| Wed, May 09, 2012 | 56A | See 33-Across | Eshan Mitra | Shortz |
| Mon, Jan 31, 2011 | 32D | Prison | Andrea Carla Michaels | Shortz |
| Sat, Nov 27, 2010 | 46A | See 33-Down | Xan Vongsathorn | Shortz |
| Thu, Sep 23, 2010 | 5A | "The Usual Suspects" setting | David J. Kahn | Shortz |
| Tue, Aug 10, 2010 | 37A | Lockup | Peter A. Collins | Shortz |
| Tue, Jun 30, 2009 | 7D | One corner of a Monopoly board | Steve Dobis | Shortz |
| Tue, Oct 07, 2008 | 55D | One corner on a Monopoly board | Kevin G. Der | Shortz |
| Wed, Jul 20, 2005 | 54D | Lockup | Roy Leban | Shortz |
| Mon, Jun 07, 2004 | 54A | Corner square in Monopoly | Lynn Lempel | Shortz |
| Mon, Nov 24, 2003 | 59A | Incarcerate | Nancy Kavanaugh | Shortz |
| Fri, Sep 05, 2003 | 27A | Cooler | Manny Nosowsky | Shortz |
| Tue, May 20, 2003 | 6D | One corner of a Monopoly board | Peter Abide | Shortz |
| Tue, Mar 04, 2003 | 39D | Monopoly corner square | Alan Arbesfeld | Shortz |
| Sun, Jan 19, 2003 | 38D | Monopoly square | Eric Berlin | Shortz |
| Wed, Jul 10, 2002 | 1A | Monopoly square | Richard Silvestri | Shortz |
| Wed, Mar 06, 2002 | 64A | Monopoly square | Richard Silvestri | Shortz |
| Wed, Jul 11, 2001 | 59A | Corner after "GO" | Richard Silvestri | Shortz |
| Wed, Dec 06, 2000 | 55D | Clink | Mel Taub (and crossword class) | Shortz |
| Fri, Aug 06, 1999 | 45A | Fine alternative | Raymond Hamel | Shortz |
| Mon, Dec 01, 1997 | 16A | Corner square in Monopoly | Mark Danna | Shortz |
| Tue, Sep 30, 1997 | 33A | Set in "Die Fledermaus" | Nancy Schuster | Shortz |
| Thu, Jul 03, 1997 | 37D | Clink | Brendan Emmett Quigley | Shortz |
| Sat, Jan 13, 1996 | 34D | Lock up | J. Page | Shortz |
| Mon, Jan 01, 1996 | 17A | Monopoly corner square | A. Klaus | Shortz |
| Sun, May 14, 1995 | 60A | Lift:elevator::bridewell:___ | Richard Silvestri | Shortz |
| Mon, Dec 12, 1994 | 59A | One corner in Monopoly | Joy L. Wouk | Shortz |
| Tue, Jun 21, 1994 | 1A | Incarcerate | Betty Jorgensen | Shortz |
| Sun, Mar 13, 1994 | 55D | "Go directly to ___" | Nancy Nicholson Joline | Shortz |