| Date | Grid | Clue | Author |
| Mon Apr 8, 2024 | 56A | This emoji: 🤓 | Peter Gordon |
| Tue Mar 26, 2024 | 38A | Techie or Trekkie, say | Laura Dershewitz and Katherine Baicker |
| Fri Jan 26, 2024 | 13D | Many a Comic-Con attendee | Sarah Sinclair and Rafael Musa |
| Wed Oct 11, 2023 | 61D | Wonk | Miranda Kany |
| Tue Jul 25, 2023 | 7D | Person who might do the Vulcan salute | Gary Larson and Doug Peterson |
| Sun Apr 9, 2023 | 25A | Trivia lover, maybe | John Ewbank |
| Mon Jan 16, 2023 | 12D | Self-description for a D&D enthusiast, maybe | Michael Paleos |
| Tue Oct 18, 2022 | 38D | Brainy oddball | Dan Schoenholz |
| Sun Jul 24, 2022 | 65A | Square type (3) | Jessie Trudeau and Ross Trudeau |
| Tue Apr 12, 2022 | 38D | Wonkish sort (2) | Dan Schoenholz |
| Tue Feb 1, 2022 | 56D | Peter Parker in "Spider-Man," for one | Zhouqin Burnikel |
| Sun Oct 31, 2021 | 13D | Fluent speaker of Elvish, say | Alex Eaton-Salners |
| Sat Sep 4, 2021 | 49D | "Jobs vs. Gates: The Hippie and the ___" (2015 TV movie) | Byron Walden |
| Fri Aug 13, 2021 | 35D | Lead-in to core or fest | John Guzzetta and Michael Hawkins |
| Sun Jul 4, 2021 | 97A | One who's able to rattle off digits of pi, perhaps | Howard Barkin |
| Sun May 23, 2021 | 61A | Sort represented by the 🤓 emoji | Jennifer Nebergall |
| Wed Feb 10, 2021 | 39D | Homework lover, say | Kate Hawkins |
| Tue Sep 29, 2020 | 32D | One who knows all the answers, maybe | Ricky Cruz |
| Mon Sep 7, 2020 | 19A | Brainy sort | Gareth Bain |
| Sun Jun 30, 2019 | 54A | Spend all weekend solving crosswords, say, with "out" | Emily Carroll |
| Tue May 28, 2019 | 5D | Superbrainy sort | Aimee Lucido |
| Fri Apr 26, 2019 | 22A | Wonkish sort (2) | Kyle Dolan |
| Mon Jul 2, 2018 | 62A | One probably not with the jocks at the lunch table | Evan Kalish |
| Wed Mar 21, 2018 | 53D | Put-down that nowadays may be worn as a badge of honor | Laura Braunstein |
| Sun Oct 29, 2017 | 29A | Get excited about crosswords, say, with "out" | Ross Trudeau |
| Sun Jun 4, 2017 | 86D | Homework lover, maybe | Tom McCoy |
| Wed Mar 22, 2017 | 63D | Jerry Lewis's "Nutty Professor" was an early example of one | Jeffrey Wechsler |
| Mon Feb 6, 2017 | 54D | Jock's antithesis | Andy Hinz |
| Fri Jan 6, 2017 | 22A | Brainiac, stereotypically | Jacob Stulberg |
| Tue Oct 4, 2016 | 57D | Do 10 crosswords in a row, say, with "out" | Sam Buchbinder |
| Mon Sep 19, 2016 | 24A | Socially maladroit sort | Zhouqin Burnikel |
| Tue Apr 12, 2016 | 25D | Dorkmeister | Alan DerKazarian |
| Wed Dec 30, 2015 | 7D | Almost any character on "The Big Bang Theory" | Mary Lou Guizzo and Jeff Chen |
| Tue Sep 1, 2015 | 5D | One scoring 100% on Sporcle quizzes, say | Michael Torch |
| Tue Jan 13, 2015 | 37A | Geek (2) | Michael Blake |
| Tue Dec 16, 2014 | 3D | One whose favorite website is Sporcle, say | Joel D. Lafargue |
| Sun Nov 9, 2014 | 75A | With 77-Across, when combined into one word, national trivia championship, e.g. | Tom McCoy |
| Thu Nov 6, 2014 | 14D | Filmdom's Napoleon Dynamite, for one | Matt Ginsberg |
| Thu Dec 5, 2013 | 19D | Napoleon Dynamite, e.g. | Dan Schoenholz |
| Wed Nov 27, 2013 | 36A | Hardly Mr. Cool (4) | Jules P. Markey |
| Wed Nov 20, 2013 | 30A | Stereotypical Mensan | Peter A. Collins |
| Tue Nov 12, 2013 | 26D | Mathlete, stereotypically (2) | Mike Doran |
| Tue Aug 27, 2013 | 63A | Weenie | Jacob McDermott |
| Sun Jul 28, 2013 | 87D | Bookworm, maybe | Andrew Reynolds |
| Sat Jul 13, 2013 | 5D | Pi Day celebrant, perhaps | Byron Walden |
| Mon Jun 3, 2013 | 30D | Stereotypical techie | John Lampkin |
| Thu May 2, 2013 | 35D | Swot : Britain :: ___ : America | Josh Knapp |
| Sun Mar 31, 2013 | 63A | Brainy person, and proud of it | Caleb Madison |
| Wed Dec 12, 2012 | 30D | Square figure | Peter A. Collins |
| Mon Nov 5, 2012 | 22D | Unlikely prom king (4) | Andrea Carla Michaels |
| Tue Sep 11, 2012 | 64A | Unlikely prom king (4) | Kenneth Leeser |
| Mon Aug 6, 2012 | 70A | Uncool sort (5) | Lynn Lempel |
| Thu Jun 14, 2012 | 63D | Dweeb (10) | Tracy Gray |
| Wed Oct 12, 2011 | 27A | Poindexter type | Gary Cee |
| Thu Oct 6, 2011 | 40D | Lover of brain games | Alan Arbesfeld |
| Tue Oct 4, 2011 | 57D | Anyone who can speak Klingon, e.g. | Dan Feyer |
| Sun Sep 25, 2011 | 16D | Quiz bowl lover, say | Paul Hunsberger |
| Thu Aug 18, 2011 | 63A | Creature in Dr. Seuss's "If I Ran the Zoo" | Kevan Choset |
| Fri Apr 8, 2011 | 51A | Unlikely prom king (4) | Joe Krozel |
| Fri Mar 11, 2011 | 8D | Square type (3) | Martin Ashwood-Smith |
| Tue Nov 30, 2010 | 13D | Dweeby sort | Kristian House |
| Sat Nov 13, 2010 | 40A | Many a character on "The Big Bang Theory" | Mark Diehl |
| Fri May 7, 2010 | 48A | High-school put-down | Tyler Hinman |
| Sat Apr 17, 2010 | 23D | One who might celebrate Pi Day | Tim Croce |
| Tue Apr 13, 2010 | 6D | Dorky sort | Alex Boisvert |
| Sun Mar 21, 2010 | 13D | Brainiac's put-down | Adam Fromm |
| Tue Jul 7, 2009 | 32D | Jock's counterpart | Lynn Lempel |
| Sat Nov 29, 2008 | 54D | Square type (3) | Barry C. Silk |
| Fri Oct 3, 2008 | 56D | Square (4) | Harvey Estes |
| Mon Sep 15, 2008 | 38D | Guy with his nose always stuck in a book | Sharon E. Petersen |
| Tue Jul 15, 2008 | 57D | Geek (2) | Leonard Williams |
| Tue Nov 27, 2007 | 4D | Social misfit (3) | Julie Ann Bowling |
| Fri Aug 10, 2007 | 32A | Bully's target, maybe | Patrick Berry |
| Thu Jul 12, 2007 | 13D | Unlikely party animal | Michael Shteyman |
| Tue Jun 12, 2007 | 37D | "Happy Days" put-down | Jonathan Gersch |
| Thu May 17, 2007 | 48A | Studious sort, and proud of it | Alan Arbesfeld |
| Wed May 2, 2007 | 24A | Geeky guy | Richard Silvestri |
| Sun Dec 10, 2006 | 67D | Eggheady sort (2) | David J. Kahn |
| Sat May 6, 2006 | 21D | Whom a bully may bully | James E. Buell |
| Mon Nov 21, 2005 | 70A | Overly bookish sort (2) | Wesley Johnson |
| Wed Oct 12, 2005 | 72A | Uncool sort (5) | Paul Guttormsson |
| Tue Oct 4, 2005 | 30D | Encyclopedia reader from A to Z, say | Barry C. Silk |
| Sun Jul 31, 2005 | 66D | Mathlete, stereotypically (2) | Mark Feldman |
| Mon Jun 6, 2005 | 4D | Dweeb (10) | Raymond Hamel |
| Tue May 24, 2005 | 62A | Uncool sort (5) | Mike Torch |
| Sun Mar 20, 2005 | 70D | Unlikely prom king (4) | Patrick Berry |
| Wed Mar 9, 2005 | 47A | Geeky sort (2) | Rob Richardson |
| Wed Dec 1, 2004 | 50D | Hardly Mr. Cool (4) | Roy Leban |
| Mon Nov 29, 2004 | 69A | Geeky sort (2) | Kendall Twigg and Nancy Salomon |
| Sun Oct 24, 2004 | 41D | Typical Rick Moranis film role | Patrick Berry |
| Sat Sep 4, 2004 | 24A | Social bungler | Patrick Berry |
| Tue May 11, 2004 | 56D | One who's unhip | Lee Glickstein and Nancy Salomon |
| Tue Feb 17, 2004 | 7D | Dork (2) | Bob Frank and Nancy Salomon |
| Thu Oct 9, 2003 | 43D | Square (4) | Alan Arbesfeld |
| Mon Jul 14, 2003 | 57D | Dweeb (10) | Elizabeth C. Gorski |
| Mon Sep 16, 2002 | 61A | Socially challenged person (2) | Roy Leban |
| Tue Aug 20, 2002 | 34A | Social misfit (3) | Bob Peoples |
| Fri May 17, 2002 | 59A | Computer ___ (2) | Joe DiPietro |
| Sun Mar 10, 2002 | 114A | Doofus | Nelson Hardy |
| Sun Dec 9, 2001 | 113D | Bully's prey, traditionally | Cathy Millhauser |
| Mon Nov 26, 2001 | 47A | Unhip person | Bette Sue Cohen |
| Sat Jul 14, 2001 | 29A | Role in many teen flicks | David J. Kahn |
| Mon Dec 11, 2000 | 31D | Dweeb (10) | Myles Callum |
| Mon Nov 20, 2000 | 7D | Dweeb (10) | Randall J. Hartman |
| Fri Nov 10, 2000 | 47D | Unpopular sort | Bob Klahn |
| Thu Oct 5, 2000 | 58D | Bully's prey, often | Cathy Millhauser |
| Tue Jun 6, 2000 | 2D | Doofus-y sort | Alan Arbesfeld |
| Mon Jun 5, 2000 | 40A | Dweeb (10) | William A. Ballard |
| Thu May 11, 2000 | 13D | Dateless sort | Peter Abide |
| Mon May 1, 2000 | 13D | Mr. Uncool | Gregory E. Paul |
| Sun Jan 30, 2000 | 66D | Square (4) | Peter Gordon |
| Sun Nov 21, 1999 | 97A | Propeller-head | Patrick D. Berry |
| Sun Oct 24, 1999 | 10A | Unlikely class president | Nancy Salomon |
| Sun Aug 8, 1999 | 42A | Socially challenged person (2) | Brendan Emmett Quigley |
| Thu Jul 22, 1999 | 5D | Unlikely candidate for prom king (2) | M. Preston Sherwood |
| Tue May 18, 1999 | 31D | Unlikely candidate for prom king (2) | Cynthia Joy Higgins |
| Mon May 17, 1999 | 20A | Person who gets picked on | Ethan Cooper |
| Sun May 16, 1999 | 176A | Computer ___ (2) | Nancy Nicholson Joline |
| Tue Apr 20, 1999 | 33D | Internet addict, perhaps | Elizabeth C. Gorski |
| Sun Apr 18, 1999 | 38D | One who isn't in | Frank Longo |
| Tue Apr 13, 1999 | 28D | Uncool sort (5) | Fred Piscop |
| Mon Apr 5, 1999 | 13D | Dilbert, e.g. | Gregory E. Paul |
| Wed Mar 3, 1999 | 29A | Overly brainy sort | Rich Norris |
| Fri Feb 26, 1999 | 50A | This may be hard to date | Martin Ashwood-Smith |
| Mon Jan 18, 1999 | 37D | One who's socially clueless | Frederick T. Buhler |
| Mon Jan 4, 1999 | 13D | Uncool one | Gregory E. Paul |
| Tue Nov 3, 1998 | 64A | Hardly Mr. Cool (4) | Ed Early |
| Sun Oct 18, 1998 | 17D | Hardly a hipster | David J. Kahn |
| Sun Sep 27, 1998 | 17D | Social misfit (3) | Randolph Ross |
| Mon Sep 7, 1998 | 71A | Brainy, socially inept sort | Gregory E. Paul |
| Mon Jul 6, 1998 | 57D | Uncool sort (5) | Sheldon Benardo |
| Wed May 27, 1998 | 38D | Disappointing date, maybe | Mark Elliot Skolsky |
| Wed Mar 18, 1998 | 65D | Bookworm | Susan Smith |
| Wed Feb 11, 1998 | 61A | Overly bookish sort (2) | Nancy S. Ross |
| Mon Oct 27, 1997 | 37A | Dweeb (10) | Mark Gottlieb |
| Sun Oct 12, 1997 | 83A | Dweeb (10) | Nancy Salomon |
| Tue Jul 1, 1997 | 31D | Taped eyeglasses wearer | Fred Piscop |
| Sun Jun 29, 1997 | 48D | Square (4) | David J. Kahn |
| Thu Apr 17, 1997 | 11D | Square, updated | Susan Smith |
| Tue Mar 25, 1997 | 17A | One socially challenged | Brendan Emmett Quigley |
| Mon Feb 3, 1997 | 35A | Eggheady sort (2) | M. E. Brindamour |
| Tue Dec 19, 1995 | 21D | Dork (2) | Marie Heller |
| Fri Sep 15, 1995 | 13D | Teen outcast | Matt Gaffney |
| Thu Jun 8, 1995 | 51D | Dweeb (10) | Chuck Deodene |
| Mon Apr 3, 1995 | 12D | Uncool fellow | Randall J. Hartman |
| Sat Jan 28, 1995 | 28A | One who's not in (2) | Randolph Ross |
| Mon Jan 16, 1995 | 14A | One who's socially challenged | Walter Covell |
| Thu Nov 3, 1994 | 65A | Dweeb (10) | Cathy Millhauser |
| Fri Oct 14, 1994 | 41D | One who's not in (2) | Bob Sefick |
| Mon Oct 10, 1994 | 69A | Hardly Mr. Cool (4) | Wayne Robert Williams |
| Sun Apr 24, 1994 | 103A | Common butt of jokes | Louis Sabin |
| Mon Dec 6, 1993 | 11D | Wonk, maybe | Peter Gordon |