| Date | Grid | Clue | Author |
| Wed Apr 26, 2023 | 34D | Novelist Philip (2) | Aaron M. Rosenberg |
| Wed Aug 17, 2022 | 26D | With 35-Down, savings plan option | Michael Paleos |
| Fri Jul 29, 2022 | 45A | Retirement plan, informally | Robyn Weintraub |
| Sat Apr 2, 2022 | 46A | Veronica ___, author of the "Divergent" trilogy | Kyle Dolan |
| Sun Nov 28, 2021 | 74A | After-tax investment account, informally | Jeff Kremer |
| Wed Dec 9, 2020 | 6D | "Divergent" author Veronica | Owen Travis and Jeff Chen |
| Sat Jun 20, 2020 | 21D | Big name in retirement accounts | Stella Zawistowski |
| Thu Apr 2, 2020 | 45A | Philip who wrote "American Pastoral" | Evan Mahnken |
| Thu Oct 31, 2019 | 2D | Kind of I.R.A. (2) | Ezra Brauner and Jeff Chen |
| Mon Oct 7, 2019 | 11D | ___ I.R.A. (2) | Keiran King |
| Sun Aug 25, 2019 | 17D | Retirement account option, informally | Matt Ginsberg |
| Sat Jun 15, 2019 | 53A | Rocker David Lee ___ (2) | Ryan McCarty |
| Wed Apr 17, 2019 | 1A | Veronica ___, author of the best-selling "Divergent" series | Alison Ohringer and Erik Agard |
| Sun Dec 3, 2017 | 39A | Philip who wrote "Portnoy's Complaint" | David Steinberg |
| Wed Feb 15, 2017 | 51D | Philip who said "goodbye" to Columbus | Jesse Eisenberg and Patrick Blindauer |
| Wed Feb 1, 2017 | 2D | Kind of I.R.A. (2) | Matthew Sewell and Jeff Chen |
| Wed Jun 15, 2016 | 37D | Hyman ___, main antagonist in "The Godfather Part II" | Jason Flinn |
| Sun Mar 1, 2015 | 83D | Senator William who pioneered a type of I.R.A. | Finn Vigeland |
| Wed Aug 6, 2014 | 14A | Singer David Lee ___ | Brendan Emmett Quigley |
| Thu Jul 24, 2014 | 58A | Writer Philip (2) | David Phillips |
| Sat Apr 5, 2014 | 25D | With 29-Across, nest egg choice | Ashton Anderson and James Mulhern |
| Sun Jun 16, 2013 | 24D | Horror director Eli | Mel Rosen |
| Wed Oct 12, 2011 | 57A | Novelist Philip (2) | Gary Cee |
| Tue Dec 14, 2010 | 53D | "Letting Go" novelist Philip | Mark Feldman |
| Wed Sep 29, 2010 | 43A | Author Philip | Charles Gersch |
| Sun Nov 1, 2009 | 18D | "The Human Stain" novelist (3) | Matt Ginsberg and Pete Muller |
| Wed Sep 16, 2009 | 48A | "Portnoy's Complaint" author (5) | Maura B. Jacobson |
| Fri Aug 14, 2009 | 43A | "The Human Stain" novelist (3) | Barry C. Silk |
| Wed Jun 24, 2009 | 19A | Rock's David Lee ___ | Corey Rubin |
| Mon May 18, 2009 | 47A | ___ I.R.A. (savings plan for old age) | Billie Truitt |
| Mon Feb 16, 2009 | 39A | Philip who wrote "Goodbye, Columbus" | David Kwong |
| Fri Dec 19, 2008 | 38A | Longtime Delaware senator William (2) | Natan Last |
| Mon Jun 16, 2008 | 14A | ___ I.R.A. (investment) | Ronald J. and Nancy J. Byron |
| Fri Mar 30, 2007 | 11A | "The Human Stain" novelist (3) | David Quarfoot |
| Sun Aug 6, 2006 | 38D | "Zuckerman Unbound" novelist (2) | Mark Feldman |
| Tue Mar 7, 2006 | 2D | ___ I.R.A. (2) | Richard Jacobs |
| Mon Dec 13, 2004 | 46A | Rocker David Lee ___ (2) | Sarah Keller |
| Fri Jul 30, 2004 | 42A | Longtime Delaware senator William (2) | Manny Nosowsky |
| Wed Apr 7, 2004 | 23D | "Portnoy's Complaint" author (5) | Nancy Salomon |
| Mon Mar 22, 2004 | 49A | Writer Philip (2) | Kyle Mahowald |
| Sun May 12, 2002 | 37D | "Letting Go" novelist (2) | Alan Arbesfeld |
| Sun Jan 20, 2002 | 46D | "The Dying Animal" novelist | Brendan Emmett Quigley |
| Sun Jan 7, 2001 | 87A | "Just a Gigolo" singer, 1985 | Manny Nosowsky |
| Sun Jun 11, 2000 | 123A | ___ v. United States (classic Supreme Court obscenity case) | Nelson Hardy |
| Fri May 19, 2000 | 58A | Longtime Delaware senator (2) | Martin Ashwood-Smith |
| Mon Apr 24, 2000 | 66A | "Portnoy's Complaint" author (5) | Peter Gordon |
| Thu Apr 13, 2000 | 2D | "Goodbye Columbus" author (2) | Matt Gaffney |
| Sun Oct 31, 1999 | 85A | "Zuckerman Unbound" novelist (2) | Frank A. Longo |
| Wed Feb 24, 1999 | 31A | Longtime Delaware Senator (2) | Mark Elliot Skolsky |
| Tue Sep 15, 1998 | 49D | "Portnoy's Complaint" author (5) | Gilbert H. Ludwig |
| Sat Dec 20, 1997 | 36D | "Call It Sleep" novelist | Rich Norris |
| Fri Mar 1, 1996 | 53A | Delaware Senator William | Charles E. Gersch |
| Sun Oct 8, 1995 | 31D | "Letting Go" novelist (2) | Nancy Nicholson Joline |
| Mon Feb 13, 1995 | 67A | "Portnoy's Complaint" author (5) | Sidney L. Robbins |
| Wed Dec 21, 1994 | 21D | "Goodbye, Columbus" author (2) | Alfio Micci |
| Tue May 3, 1994 | 16A | Portnoy's creator | Lois Sidway |