| Date | Grid | Clue | Author | Editor |
| Sun Apr 14, 2024 | 113D | Monopoly set, for short | John Rippe and Jeff Chen | Fagliano |
| Wed Mar 15, 2023 | 65D | B&O and others (5) | Michael B. Berg | Shortz |
| Sun Nov 20, 2022 | 13D | Monopoly properties that don't get hotels, for short | Joe Deeney | Shortz |
| Sun Oct 9, 2022 | 113D | B&O and Reading: Abbr. (3) | Jessie Trudeau and Ross Trudeau | Shortz |
| Tue Jan 4, 2022 | 56D | B&O and Short Line: Abbr. (2) | David Bukszpan | Shortz |
| Mon Dec 6, 2021 | 32D | $200 Monopoly properties: Abbr. (3) | Emily Rourke | Shortz |
| Sun Aug 15, 2021 | 75A | Some $200 Monopoly properties, in brief | Aimee Lucido and Ella Dershowitz | Shortz |
| Sat Dec 5, 2020 | 52D | $200 Monopoly properties, for short | Brendan Emmett Quigley | Shortz |
| Mon Aug 31, 2020 | 41A | Monopoly properties you can't put houses on, in brief | Anne Marie Crinnion | Shortz |
| Thu Apr 2, 2020 | 25D | Monopoly quartet: Abbr. (10) | Evan Mahnken | Shortz |
| Sun Dec 22, 2019 | 49D | Monopoly quartet: Abbr. (10) | Laura Taylor Kinnel | Shortz |
| Sun Jan 20, 2019 | 79A | Monopoly foursome: Abbr. (4) | Richard Crowe | Shortz |
| Thu Oct 26, 2017 | 44D | Norfolk Southern and others: Abbr. | Jacob Stulberg | Shortz |
| Thu Jun 15, 2017 | 30D | B&O and others: Abbr. | Richard F. Mausser | Shortz |
| Thu Dec 15, 2016 | 30D | Lines on some maps: Abbr. | Jacob Stulberg | Shortz |
| Sat Sep 24, 2016 | 54A | Pennsylvania and others: Abbr. (2) | Mary Lou Guizzo | Shortz |
| Mon Sep 12, 2016 | 46A | Monopoly game's B&O and Reading: Abbr. | Victor Fleming and Andrea Carla Michaels | Shortz |
| Tue Jul 5, 2016 | 26D | B&O and Pennsylvania: Abbr. | Jules Markey | Shortz |
| Wed May 4, 2016 | 23A | Employers of dispatchers and brakemen: Abbr. | Jacob Stulberg | Shortz |
| Fri Apr 1, 2016 | 50A | Pennsylvania and others: Abbr. (2) | Peter Gordon | Shortz |
| Wed Nov 11, 2015 | 21A | B&O and Pennsylvania, in Monopoly | David Steinberg | Shortz |
| Thu Jun 25, 2015 | 46D | Pennsylvania and Erie, once: Abbr. | David Poole | Shortz |
| Wed May 13, 2015 | 35D | Monopoly quartet: Abbr. (10) | Jeffrey Wechsler | Shortz |
| Thu Dec 4, 2014 | 23D | Transportation lines: Abbr. | Kacey Walker and David Quarfoot | Shortz |
| Fri Apr 18, 2014 | 61D | Monopoly quartet: Abbr. (10) | James Mulhern | Shortz |
| Wed Jun 19, 2013 | 30A | Some Monopoly properties: Abbr. | Richard F. Mausser | Shortz |
| Sun Feb 17, 2013 | 105A | B&O and others (5) | Ian Livengood and J.A.S.A. Crossword Class | Shortz |
| Fri Jan 18, 2013 | 35D | They have end-to-end cars: Abbr. | Tim Croce | Shortz |
| Sun Mar 4, 2012 | 13D | They make 39-Down: Abbr. | David J. Kahn | Shortz |
| Sun Dec 18, 2011 | 123A | Lines with crossings: Abbr. | Patrick Merrell | Shortz |
| Mon Sep 5, 2011 | 21D | Four Monopoly properties: Abbr. (3) | Patrick Merrell | Shortz |
| Sat Aug 27, 2011 | 26A | Their lines have ties: Abbr. | Ashton Anderson | Shortz |
| Thu Jun 2, 2011 | 6D | Ones on the right track?: Abbr. | Brendan Emmett Quigley | Shortz |
| Wed Dec 29, 2010 | 38D | $200 Monopoly properties: Abbr. (3) | Patrick Merrell | Shortz |
| Mon Dec 13, 2010 | 14D | B&O and Short Line: Abbr. (2) | Patrick Blindauer | Shortz |
| Mon Aug 23, 2010 | 35A | Four Monopoly assets: Abbr. | Oliver Hill | Shortz |
| Sat May 29, 2010 | 59D | Yards are part of them: Abbr. | Caleb Madison | Shortz |
| Sun May 2, 2010 | 76A | Rock Island and Reading: Abbr. | Kelsey Blakley | Shortz |
| Thu Jan 21, 2010 | 35D | Things with xings | Elizabeth C. Gorski | Shortz |
| Mon Dec 28, 2009 | 62D | B&O and Reading: Abbr. (3) | Patrick Merrell | Shortz |
| Tue Nov 10, 2009 | 57D | $200 Monopoly properties: Abbr. (3) | Alan Arbesfeld | Shortz |
| Wed Jul 16, 2008 | 3D | Purview of the I.C.C. | Joe Krozel | Shortz |
| Thu Jun 19, 2008 | 25A | Monopoly quartet: Abbr. (10) | Joe Krozel | Shortz |
| Fri Jun 6, 2008 | 32A | Commuting choices: Abbr. | Ashish Vengsarkar | Shortz |
| Fri Oct 5, 2007 | 54D | Commuters' choices: Abbr. | Lynn Lempel | Shortz |
| Fri Aug 31, 2007 | 46A | Regulation targets for Theodore Roosevelt: Abbr. | Paula Gamache | Shortz |
| Sun Jun 10, 2007 | 118A | Reading and others: Abbr. (2) | Bob Klahn | Shortz |
| Mon Jun 4, 2007 | 58D | Monopoly quartet: Abbr. (10) | Steve Kahn | Shortz |
| Mon Apr 9, 2007 | 40D | B. & O. and Reading: Abbr. (3) | J. K. Hummel | Shortz |
| Fri Mar 9, 2007 | 57D | Traffic at Union Sta. | Randolph Ross | Shortz |
| Wed Aug 23, 2006 | 32D | Monopoly foursome: Abbr. (4) | Kevan Choset | Shortz |
| Sun May 7, 2006 | 85D | Reading and the like: Abbr. | Trip Payne | Shortz |
| Tue Jan 31, 2006 | 31A | Four Monopoly properties: Abbr. (3) | Patrick Merrell | Shortz |
| Sun Dec 4, 2005 | 31A | Monopoly quartet: Abbr. (10) | Eric Berlin and Craig Kasper | Shortz |
| Tue Oct 5, 2004 | 31D | Trains: Abbr. | James R. Leeds | Shortz |
| Sun Sep 19, 2004 | 41D | Some transp. stocks | Kyle Mahowald | Shortz |
| Sun Sep 5, 2004 | 112D | Monopoly foursome: Abbr. (4) | Patrick Merrell | Shortz |
| Sun Jul 11, 2004 | 53A | Some Xing crossers | Randolph Ross | Shortz |
| Sun Jan 25, 2004 | 59D | Monopoly grp. | Harvey Estes and Nancy Salomon | Shortz |
| Sun Jan 4, 2004 | 108D | Monopoly props. | Patrick Merrell | Shortz |
| Fri Oct 24, 2003 | 51A | They have strong ties: Abbr. | Sherry O. Blackard | Shortz |
| Sat Apr 26, 2003 | 19A | Some are underground: Abbr. | Patrick Merrell | Shortz |
| Mon Mar 31, 2003 | 35D | Monopoly quartet: Abbr. (10) | Patrick Merrell | Shortz |
| Sat Mar 22, 2003 | 4D | Where to find trainers?: Abbr. | Rich Norris | Shortz |
| Mon Dec 3, 2001 | 41A | B. & O. and others (5) | Nancy Salomon and Harvey Estes | Shortz |
| Sun Nov 18, 2001 | 81A | Some Monopoly spaces: Abbr. | Jim Page | Shortz |
| Sun Oct 28, 2001 | 119A | Short Line and others: Abbr. | Michael Ashley | Shortz |
| Sun Jun 3, 2001 | 86D | Monopoly quartet: Abbr. (10) | Bob Peoples and Nancy Salomon | Shortz |
| Sat Jan 13, 2001 | 30A | $200 purchases: Abbr. | Rich Norris | Shortz |
| Sun Dec 10, 2000 | 45D | $200 Monopoly props. | Rich Norris | Shortz |
| Wed Jun 28, 2000 | 25A | They have Xings (2) | Randy Sowell | Shortz |
| Mon May 8, 2000 | 23A | Monopoly properties: Abbr. (2) | Ed Early | Shortz |
| Sat May 6, 2000 | 44A | Subjects of interstate regulation: Abbr. | Rich Norris | Shortz |
| Wed May 3, 2000 | 69A | Monopoly acquisitions: Abbr. (2) | Nancy Salomon | Shortz |
| Mon Nov 15, 1999 | 52D | They have Xings (2) | Nick Grivas | Shortz |
| Thu Oct 21, 1999 | 64D | Monopoly foursome: Abbr. (4) | Manny Nosowsky | Shortz |
| Tue Aug 3, 1999 | 21A | Union Pacific et al.: Abbr. | Dave Tuller | Shortz |
| Sat Jun 19, 1999 | 23D | B.&O. et al. (3) | Mark Diehl | Shortz |
| Thu Nov 26, 1998 | 19D | Some Monopoly purchases: Abbr. | David J. Kahn | Shortz |
| Mon Aug 3, 1998 | 23A | B.&O. and Reading, e.g.: Abbr. | Nancy Salomon | Shortz |
| Mon Sep 22, 1997 | 22D | Four Monopoly properties: Abbr. (3) | Gregory E. Paul | Shortz |
| Sun Sep 7, 1997 | 43D | Penn Sta. traffic | Randolph Ross | Shortz |
| Mon Apr 21, 1997 | 53D | Southern Pacific and others: Abbr. | Patrick Jordan | Shortz |
| Tue Apr 15, 1997 | 11D | B.&O. et al. (3) | Jonathan Schmalzbach | Shortz |
| Fri Nov 15, 1996 | 58A | B.&O. et al. (3) | R. Norris | Shortz |
| Fri Nov 1, 1996 | 15D | Reading and others: Abbr. (2) | M. Rosen | Shortz |
| Thu Aug 22, 1996 | 39A | Monopoly properties: Abbr. (2) | R. Norris | Shortz |
| Fri Jan 12, 1996 | 11D | Some utils. | R. Norris | Shortz |
| Sun Sep 24, 1995 | 47A | Monopoly quartet: Abbr. (10) | Randolph Ross | Shortz |
| Sun Sep 10, 1995 | 28A | Monopoly landings: Abbr. | David J. Kahn | Shortz |
| Sun Aug 27, 1995 | 69D | Leland Stanford companies: Abbr. | Martin Schneider | Shortz |
| Sun Jul 16, 1995 | 83A | B.&O. and others (5) | Naomi Geller Lipsky | Shortz |
| Fri Feb 3, 1995 | 61D | Monopoly acquisitions: Abbr. (2) | Matt Gaffney | Shortz |
| Sat Dec 11, 1993 | 37D | B. & O., and others (5) | Robert H. Wolfe | Shortz |