| Date | Grid | Clue | Author | Editor |
| Sun Sep 14, 2025 | 97D | Witherspoon of "A Wrinkle in Time" | Daniel Grinberg | Shortz |
| Thu Jun 19, 2025 | 62A | Witherspoon of "Little Fires Everywhere" | Hannah Slovut-Einertson | Shortz |
| Mon Apr 21, 2025 | 30A | Actress Witherspoon (13) | Thomas van Geel | Shortz |
| Fri Mar 7, 2025 | 46D | The W.N.B.A.'s Angel ___ | Malaika Handa | Shortz |
| Mon Jan 27, 2025 | 4D | Actress Witherspoon (13) | Alexander Liebeskind | Shortz |
| Sun Jun 9, 2024 | 123A | Actress Witherspoon (13) | Zachary Schiff | Fagliano |
| Sun Dec 17, 2023 | 120A | Actress Witherspoon (13) | Jeremy Newton | Shortz |
| Fri Nov 17, 2023 | 54A | Candy mogul Harry | Hemant Mehta | Shortz |
| Mon Jul 24, 2023 | 26D | Witherspoon of "Legally Blonde" (12) | John Ewbank | Shortz |
| Sun May 14, 2023 | 20D | Witherspoon of Hollywood | Sid Sivakumar | Shortz |
| Tue Feb 14, 2023 | 55D | Witherspoon of "The Morning Show" | Ella Dershowitz | Shortz |
| Sun Nov 20, 2022 | 36A | Actress Witherspoon (13) | Joe Deeney | Shortz |
| Wed Aug 31, 2022 | 21A | Oscar winner Witherspoon | Joe Deeney | Shortz |
| Tue Feb 8, 2022 | 57A | Actress Witherspoon (13) | Adam Aaronson, Jack Joshi and Jackson Janes | Shortz |
| Sun Sep 12, 2021 | 59A | One of the brothers on "Malcolm in the Middle" | Alex Rosen | Shortz |
| Tue Apr 6, 2021 | 2D | Actress Witherspoon (13) | Amanda Chung and Karl Ni | Shortz |
| Fri May 1, 2020 | 65A | Eponym in a candy store | Trenton Charlson | Shortz |
| Sat Nov 30, 2019 | 2D | Eponymous candy man (2) | Joe Deeney | Shortz |
| Sun Jun 23, 2019 | 102D | Eponymous cup maker | David Liben-Nowell and Victor Barocas | Shortz |
| Tue Apr 30, 2019 | 21A | Actress Witherspoon (13) | Erik Agard | Shortz |
| Wed Dec 26, 2018 | 68A | Pokey or Pee Wee of Major League Baseball | Howard Barkin | Shortz |
| Fri Nov 16, 2018 | 65A | Older brother of Malcolm on "Malcolm in the Middle" | Kyle Dolan | Shortz |
| Thu Aug 9, 2018 | 26A | Candymaker H. B. ___ | Patrick Merrell | Shortz |
| Sat Mar 17, 2018 | 47D | Dodgers Hall-of-Famer whose #1 has been retired | Roland Huget | Shortz |
| Sun Oct 8, 2017 | 122A | Chocolate cup inventor H. B. ___ | Erik Agard and Alex Briñas | Shortz |
| Sun Jun 11, 2017 | 57D | Witherspoon of "Legally Blonde" (12) | Charles M. Deber | Shortz |
| Tue Dec 6, 2016 | 61A | Witherspoon of "Four Christmases" | Ed Sessa | Shortz |
| Sun Jul 17, 2016 | 99D | Candy man (3) | Jerry Miccolis | Shortz |
| Fri Jul 8, 2016 | 37A | He worked for Hershey in the 1910s-'20s | Barry C. Silk | Shortz |
| Wed Feb 3, 2016 | 44D | Witherspoon of "Legally Blonde" (12) | Tom McCoy | Shortz |
| Sun Dec 27, 2015 | 116A | Witherspoon of "Legally Blonde" (12) | Don Gagliardo and Zhouqin Burnikel | Shortz |
| Fri Dec 4, 2015 | 58A | Candy counter eponym | Martin Ashwood-Smith | Shortz |
| Fri Oct 30, 2015 | 42A | Teammate of Robinson (2) | Patrick Berry | Shortz |
| Tue Aug 18, 2015 | 33A | Kyle ___, "The Terminator" hero (4) | Bill Thompson | Shortz |
| Mon Jun 1, 2015 | 32D | Witherspoon who played 11-Down in "Walk the Line" | David Woolf | Shortz |
| Wed Apr 29, 2015 | 15A | Peanut-butter-and-chocolate innovator H. B. ___ | Daniel Landman | Shortz |
| Thu Feb 26, 2015 | 61A | Witherspoon of "Wild" | Caleb Emmons | Shortz |
| Thu Oct 16, 2014 | 12D | He wears #1 in "42" | John Farmer | Shortz |
| Sun Aug 3, 2014 | 100D | Witherspoon of "Mud" | Ian Livengood | Shortz |
| Mon Jul 28, 2014 | 67A | Baseball's Pee Wee (2) | Tom McCoy | Shortz |
| Sat Apr 19, 2014 | 27A | Candy pioneer H. B. ___ | Stu Ockman | Shortz |
| Mon Apr 14, 2014 | 27D | Witherspoon of "Legally Blonde" (12) | Gareth Bain | Shortz |
| Fri Feb 21, 2014 | 58A | Teammate of Robinson (2) | Patrick Berry | Shortz |
| Mon Jul 15, 2013 | 28D | Witherspoon of 2012's "Mud" | Jeff Chen and Angela Olson Halsted | Shortz |
| Tue Jul 9, 2013 | 55D | Eponym for a peanut butter cup | Kurt Krauss | Shortz |
| Wed Jul 3, 2013 | 28A | Witherspoon of "Walk the Line" (3) | Pamela Klawitter | Shortz |
| Tue Jun 18, 2013 | 8D | Witherspoon of "Legally Blonde" (12) | Tim Croce | Shortz |
| Thu Feb 7, 2013 | 2D | Teammate of Robinson of the 1940s-'50s Dodgers | David Levinson Wilk | Shortz |
| Mon Sep 17, 2012 | 21D | Actress Witherspoon (13) | Adam G. Perl | Shortz |
| Tue Feb 14, 2012 | 34D | Pee Wee of baseball | Paula Gamache | Shortz |
| Mon Jan 2, 2012 | 56D | Pee Wee of the 1940s-'50s Dodgers | Paula Gamache | Shortz |
| Thu Jun 30, 2011 | 36D | Kyle ___, "The Terminator" hero (4) | David Poole | Shortz |
| Mon Apr 4, 2011 | 54D | Pee Wee who befriended Jackie Robinson | Lynn Lempel | Shortz |
| Tue Sep 14, 2010 | 52D | Witherspoon of "Legally Blonde" (12) | Eshan Mitra, Brown University '12 | Shortz |
| Sun Jun 20, 2010 | 111A | Brother of Malcolm on "Malcolm in the Middle" | Todd Gross and Ashish Vengsarkar | Shortz |
| Sat Apr 17, 2010 | 32A | Candy man (3) | Tim Croce | Shortz |
| Tue Apr 6, 2010 | 51D | Witherspoon of "Legally Blonde" (12) | Sarah Keller | Shortz |
| Thu Sep 10, 2009 | 62A | Chip ___, whom many consider the greatest cash game poker player of all time | Kevan Choset | Shortz |
| Thu Jun 11, 2009 | 16D | "The Terminator" man Kyle ___ | Alex Boisvert | Shortz |
| Sun Mar 22, 2009 | 76A | Man with cups and pieces | Joon Pahk and Matt Matera | Shortz |
| Sat Dec 27, 2008 | 13D | Eponymous candy man (2) | Karen M. Tracey | Shortz |
| Sun Sep 21, 2008 | 83D | "Malcolm in the Middle" boy | Brendan Emmett Quigley | Shortz |
| Sun Jun 1, 2008 | 37D | Actress Witherspoon (13) | Patrick Berry | Shortz |
| Sun Dec 30, 2007 | 89D | Kyle ___, "The Terminator" hero (4) | Elizabeth C. Gorski | Shortz |
| Tue Dec 18, 2007 | 66A | Teammate of Snider and Hodges (2) | Alan Arbesfeld | Shortz |
| Mon Dec 3, 2007 | 31D | Witherspoon of "Walk the Line" (3) | Harvey Estes | Shortz |
| Sun Aug 26, 2007 | 70A | 1940s-'50s Dodger who was a 10-time All-Star | Andrew M. Greene and Craig Kasper | Shortz |
| Tue May 22, 2007 | 3D | Oscar-winning Witherspoon | Roger Wolff | Shortz |
| Thu May 3, 2007 | 27D | Kyle ___, "The Terminator" protagonist | Richard Chisholm | Shortz |
| Sat Mar 17, 2007 | 48D | Her "Don't You Know" was a #1 R & B hit | John Farmer | Shortz |
| Thu Feb 1, 2007 | 37D | Candy man (3) | Michael S. Maurer | Shortz |
| Thu Jan 25, 2007 | 69A | Artful Dodger (3) | Manny Nosowsky | Shortz |
| Mon Jan 22, 2007 | 71A | Songstress Della | C. W. Stewart | Shortz |
| Thu Oct 19, 2006 | 54D | The Little Colonel | Raymond C. Young | Shortz |
| Sun Aug 27, 2006 | 129A | Candymaker Harry | Seth A. Abel | Shortz |
| Thu Aug 17, 2006 | 56D | Pee Wee of the big league | Harvey Estes | Shortz |
| Mon May 29, 2006 | 50D | Witherspoon of "Walk the Line" (3) | Alex Boisvert | Shortz |
| Fri Mar 17, 2006 | 43D | Baseball's Little Colonel (4) | John Farmer | Shortz |
| Mon Jan 2, 2006 | 63A | Pee Wee who was nicknamed The Little Colonel | Linda Schechet Tucker | Shortz |
| Thu Dec 15, 2005 | 12D | Originator of a popular peanut butter cup | Patrick Merrell | Shortz |
| Sat Sep 10, 2005 | 22A | Candy manufacturer Harry (4) | David J. Kahn | Shortz |
| Tue Aug 30, 2005 | 1D | Witherspoon of "Vanity Fair" | Leonard Williams | Shortz |
| Tue Aug 16, 2005 | 26D | Witherspoon of "Legally Blonde" (12) | Randall J. Hartman | Shortz |
| Fri Jun 24, 2005 | 63A | 1940's-50's All-Star who got his nickname from a kind of marble | Eric Berlin | Shortz |
| Wed Sep 29, 2004 | 66A | Actress Witherspoon (13) | Verna Suit | Shortz |
| Mon Apr 5, 2004 | 25A | Witherspoon of "Legally Blonde" (12) | Jim Hyres | Shortz |
| Sun Mar 14, 2004 | 143A | Eponymous candy manufacturer Harry | Craig Kasper | Shortz |
| Wed Jan 28, 2004 | 40A | Actress Witherspoon (13) | Jim Hyres | Shortz |
| Thu Jan 1, 2004 | 21A | Shortstop of fame | Richard Silvestri | Shortz |
| Sat Nov 29, 2003 | 57A | "Don't You Know" hitmaker, 1959 | Randolph Ross | Shortz |
| Wed Jul 16, 2003 | 52D | Baseball's Pee Wee (2) | Norm Guggenbiller | Shortz |
| Wed Jul 2, 2003 | 12D | Witherspoon of "Legally Blonde" (12) | Barbara Olson | Shortz |
| Fri Jun 6, 2003 | 19A | Piece maker (2) | Randolph Ross | Shortz |
| Wed Apr 30, 2003 | 52D | Snider teammate | Jerry E. Rosman | Shortz |
| Thu Mar 27, 2003 | 41D | Teammate of Snider and Hodges (2) | David J. Kahn | Shortz |
| Thu Dec 19, 2002 | 37D | Kyle ___, "The Terminator" hero (4) | Patrick Berry | Shortz |
| Wed Oct 23, 2002 | 66A | "Touched By an Angel" co-star (4) | Nancy Salomon and Nancy T. Shack | Shortz |
| Wed Aug 21, 2002 | 71A | Ebbets Field hero | Joel Kaplow | Shortz |
| Sun Aug 11, 2002 | 97D | Old Ebbets Field hero | Harvey Estes and Nancy Salomon | Shortz |
| Thu Jun 27, 2002 | 27D | Hall-of-Fame shortstop | James R. Leeds | Shortz |
| Wed Jun 12, 2002 | 70A | Certain cup maker | Nancy Salomon and Bill Zais | Shortz |
| Thu Jun 6, 2002 | 49D | Actress Witherspoon (13) | Patrick Merrell | Shortz |
| Thu May 30, 2002 | 46A | Brooklyn Dodgers great | Peter Gordon | Shortz |
| Sun Apr 14, 2002 | 7D | Peewee who wasn't so small | David J. Kahn | Shortz |
| Mon Mar 11, 2002 | 10D | Baseball great Pee Wee | Peter Gordon | Shortz |
| Tue Feb 5, 2002 | 49A | "Touched By an Angel" star Della | Alan J. Weiss | Shortz |
| Fri Dec 21, 2001 | 41A | "Touched By an Angel" co-star (4) | William I. Johnston | Shortz |
| Tue Aug 14, 2001 | 71A | Witherspoon of "Legally Blonde" (12) | Randall J. Hartman | Shortz |
| Wed Jul 18, 2001 | 4D | Poet Lizette Woodworth ___ | Elizabeth C. Gorski | Shortz |
| Wed Jun 13, 2001 | 36A | One of the Boys of Summer | Nick Grivas | Shortz |
| Thu Dec 21, 2000 | 37A | Artful Dodger? (3) | Manny Nosowsky | Shortz |
| Mon Jun 19, 2000 | 33D | Dodger shortstop of old | Manny Nosowsky | Shortz |
| Thu Apr 6, 2000 | 66A | Airbase near Lubbock (2) | Manny Nosowsky | Shortz |
| Wed Oct 6, 1999 | 21D | Artful Dodger (3) | Fred Piscop | Shortz |
| Tue Aug 24, 1999 | 15A | "Touched by an Angel" co-star (4) | Elizabeth C. Gorski | Shortz |
| Wed Aug 4, 1999 | 34D | Baseball's Little Colonel (4) | Richard Silvestri | Shortz |
| Mon May 24, 1999 | 23D | Pee Wee of the Dodgers | Gregory E. Paul | Shortz |
| Mon May 10, 1999 | 66A | "Don't You Know" singer Della | Frances Hansen | Shortz |
| Tue Jun 16, 1998 | 52D | Dodger Hall-of-Famer | Bill Ballard | Shortz |
| Sat Mar 14, 1998 | 37D | 40's-50's Dodger great | Ed Pegg Jr. | Shortz |
| Fri Mar 13, 1998 | 24D | Candy manufacturer Harry (4) | Shannon Burns | Shortz |
| Mon Feb 23, 1998 | 34A | Della of "Touched by an Angel" | Mark Danna | Shortz |
| Wed Dec 31, 1997 | 40A | "Don't You Know" singer (3) | Alfio Micci | Shortz |
| Mon Nov 24, 1997 | 46D | Shortstop Pee Wee | Alex K. Justin | Shortz |
| Tue Oct 21, 1997 | 49D | Singer Della (3) | Elizabeth C. Gorski | Shortz |
| Sat Aug 23, 1997 | 55A | Candy manufacturer Harry (4) | Rich Norris | Shortz |
| Sun Jul 6, 1997 | 93D | "Touched by an Angel" co-star (4) | Robert H. Wolfe | Shortz |
| Sun May 11, 1997 | 44A | Candy counter name | Nancy Nicholson Joline | Shortz |
| Mon Jan 27, 1997 | 34D | Pee Wee of Ebbets Field | F. Piscop | Shortz |
| Tue May 28, 1996 | 19A | Della or Pee Wee | J. R. Bender | Shortz |
| Tue Apr 16, 1996 | 54D | 40's-50's Dodger star | G. E. Paul | Shortz |
| Sun Mar 3, 1996 | 89A | Baseball's Little Colonel (4) | B. Klahn | Shortz |
| Sun Jan 28, 1996 | 7D | Pee Wee of Cooperstown | M. W. Perry | Shortz |
| Fri Nov 24, 1995 | 33D | "Don't You Know" songstress | Bob Klahn | Shortz |
| Wed Oct 18, 1995 | 33D | "The Boys of Summer" shortstop | Nancy S. Ross | Shortz |
| Wed Sep 20, 1995 | 22A | Piece-maker? (2) | Randy Sowell | Shortz |
| Sat Sep 2, 1995 | 63A | Air base near Lubbock (2) | Manny Nosowsky | Shortz |
| Thu Aug 10, 1995 | 25D | "Don't You Know" singer (3) | Matt Gaffney | Shortz |
| Tue Apr 18, 1995 | 17D | Singer Della (3) | Christopher Page | Shortz |
| Tue Apr 11, 1995 | 32D | Pee Wee ____ | Gregory E. Paul | Shortz |
| Mon Jan 23, 1995 | 53D | Della of pop | Sidney L. Robbins | Shortz |
| Sun Dec 4, 1994 | 23A | Baseball's Little Colonel (4) | Robert H. Wolfe | Shortz |
| Fri Sep 23, 1994 | 7D | Candy manufacturer Harry (4) | Bryant White | Shortz |
| Sun Apr 10, 1994 | 125D | "Don't You Know?" singer, 1959 | Trip Payne | Shortz |
| Sun Feb 13, 1994 | 57D | "Don't You Know" singer (3) | Cathy Millhauser | Shortz |
| Wed Jan 19, 1994 | 33D | Teammate of Robinson and Hodges | Stanley Newman | Shortz |
| Sat Jan 8, 1994 | 40D | Hall of Fame Dodger | Rand H. Burns | Shortz |
| Thu Dec 16, 1993 | 13D | Singer Della (3) | Nancy Joline | Shortz |
| Mon Nov 29, 1993 | 40D | Hall-of-Famer Pee Wee | Sidney L. Robbins | Shortz |