| Date | Grid | Clue | Author |
| Sat Nov 18, 2023 | 2D | ___ Jackson Jr., actor who portrayed his father in "Straight Outta Compton" | Hoang-Kim Vu |
| Mon Aug 15, 2022 | 57D | Irish surname that anagrams to A SHOE | Simon Marotte |
| Wed Jul 14, 2021 | 51D | Tony nominee Milo | Amanda Rafkin and Ross Trudeau |
| Wed Jun 16, 2021 | 10D | ___ Jackson, a.k.a. Ice Cube (2) | Finn Vigeland |
| Wed Oct 7, 2020 | 15A | ___ Jackson Jr., "Straight Outta Compton" star | Ross Trudeau |
| Fri Sep 27, 2019 | 26D | ___ Jackson, real name of Ice Cube | Jack Mowat |
| Sun May 6, 2018 | 42A | Actor Milo (19) | Brendan Emmett Quigley |
| Mon Apr 30, 2018 | 48D | Actor Milo (19) | Bruce Haight |
| Sun Dec 3, 2017 | 20A | Milo of "Romeo and Juliet," 1968 | David Steinberg |
| Mon Jul 24, 2017 | 44A | Milo of "The Verdict" (6) | Peter Gordon |
| Wed Jan 25, 2017 | 30A | Milo of "The Verdict" (6) | Tracy Gray |
| Sun Sep 25, 2016 | 99D | Actor Milo (19) | Jim Holland and Jeff Chen |
| Sun Mar 27, 2016 | 71A | Milo of stage and screen | Patrick Blindauer |
| Wed Dec 23, 2015 | 12D | "Ulysses" actor Milo | Jim Peredo |
| Wed Apr 30, 2014 | 31A | Milo of "Ulysses" (4) | Zhouqin Burnikel |
| Mon Nov 18, 2013 | 52D | Milo of "The Verdict" (6) | Edgar Fontaine |
| Tue Oct 22, 2013 | 22A | Actor Milo (19) | Kevan Choset |
| Wed Apr 10, 2013 | 54D | Milo of "The Verdict" (6) | Julian Lim |
| Sat Nov 5, 2011 | 23A | "Ulysses" star, 1967 | Kurt Mueller |
| Sat Dec 4, 2010 | 52D | Tony-winning Tessie | Doug Peterson |
| Tue Jun 8, 2010 | 19A | Milo of "Romeo and Juliet" | Peter A. Collins |
| Wed Jun 2, 2010 | 33D | Milo of "The Playboys" | Adam Cohen |
| Mon Jan 25, 2010 | 31D | Milo of "Ulysses" (4) | Holden Baker |
| Sun Feb 22, 2009 | 50D | Milo of "The Verdict," 1982 (2) | Barry C. Silk & Doug Peterson |
| Thu Dec 25, 2008 | 25D | Dublin-born film star Milo | Eric Tentarelli |
| Wed Aug 20, 2008 | 27D | Milo of Hollywood | Allan E. Parrish |
| Sun Mar 2, 2008 | 122A | Ice Cube né ___ Jackson | Patrick Blindauer and Tony Orbach |
| Sun Feb 24, 2008 | 82A | Milo of "Ulysses" (4) | Nancy Nicholson Joline |
| Tue Jul 17, 2007 | 55A | Actor Milo (19) | Natan Last |
| Tue Jan 16, 2007 | 25D | Actor Milo (19) | Dave Mackey |
| Mon Dec 25, 2006 | 22A | Actor Milo (19) | Adam G. Perl |
| Mon Jan 9, 2006 | 28D | Actor Milo (19) | Allan E. Parrish |
| Wed Dec 14, 2005 | 45D | "The Verdict" actor, 1982 | James R. Leeds |
| Tue Dec 13, 2005 | 39D | Milo of "Barbarella" (3) | Roy Leban |
| Tue Sep 13, 2005 | 33A | Milo of "Ulysses" (4) | Stella Daily and Bruce Venzke |
| Sun Apr 3, 2005 | 22A | ___ Jackson, a k a Ice Cube (2) | Nancy Nicholson Joline |
| Mon Mar 7, 2005 | 12D | Actor Milo (19) | Christina Houlihan Kelly |
| Mon Jan 24, 2005 | 15A | Irish-born actor Milo (2) | Sarah Keller |
| Tue Dec 7, 2004 | 30D | Milo of "Barbarella" (3) | David Diefendorf |
| Wed Nov 10, 2004 | 16A | Actor Milo (19) | David J. Kahn |
| Sun Oct 3, 2004 | 103D | Milo of "The Verdict," 1982 (2) | Randolph Ross |
| Mon Mar 29, 2004 | 6D | Actor Milo (19) | Barry Silk |
| Mon Nov 17, 2003 | 54D | Irish-born actor Milo (2) | Sarah Keller |
| Sun Sep 28, 2003 | 55A | Comic actress Tessie (2) | Brendan Emmett Quigley |
| Tue Sep 2, 2003 | 64A | Actor Milo (19) | Ed Early |
| Wed Apr 30, 2003 | 2D | Actor Milo (19) | Jerry E. Rosman |
| Sun Jan 26, 2003 | 106D | Milo of "Ulysses," 1967 | Nancy Salomon and Bob Peoples |
| Sun Aug 11, 2002 | 76A | Milo of "Only the Lonely," 1991 | Harvey Estes and Nancy Salomon |
| Wed May 29, 2002 | 4D | Actor Milo (19) | Alan Olschwang |
| Wed Nov 7, 2001 | 55A | Michael who starred in TV's "It's a Great Life" | Brendan Emmett Quigley |
| Thu Sep 27, 2001 | 26D | Kitty ___ (mistress in Irish history) | Manny Nosowsky |
| Wed Jun 27, 2001 | 14A | Milo or Tessie (2) | Michael Shteyman |
| Mon May 28, 2001 | 29D | Milo of "The Verdict" (6) | Gregory E. Paul |
| Tue Dec 19, 2000 | 8D | Milo of "The Verdict" (6) | Fred Piscop |
| Wed Sep 20, 2000 | 53D | Actor Milo (19) | Edgar R. Fontaine |
| Sat Sep 11, 1999 | 31D | Comic actress Tessie (2) | Rich Norris |
| Mon Sep 6, 1999 | 54D | Actor Milo (19) | Manny Nosowsky |
| Tue Jun 1, 1999 | 14A | Actor Milo (19) | Myles Callum |
| Tue Dec 1, 1998 | 48D | Milo or Tessie (2) | Stephanie Spadaccini |
| Mon Oct 12, 1998 | 27D | Actor Milo or Michael | Richard Chisholm |
| Tue Jun 23, 1998 | 48D | Actor Milo (19) | Rich Norris |
| Sun May 25, 1997 | 38A | Character actress Tessie | Cathy Millhauser |
| Sun Apr 13, 1997 | 46A | Milo of "Barbarella" (3) | Cathy Millhauser |
| Tue Apr 8, 1997 | 53D | Actor Milo (19) | Fred Piscop |
| Sun Dec 8, 1996 | 21A | 1982 Tony nominee Milo | A. J. Santora |
| Sun Jan 1, 1995 | 112A | Tony nominee for "Mass Appeal" | Henry Hook |