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| Date | Grid | Clue | Author |
|---|---|---|---|
| Wednesday, April 10, 2013 | 54D | Milo of "The Verdict" (3) | Julian Lim |
| Saturday, November 5, 2011 | 23A | "Ulysses" star, 1967 | Kurt Mueller |
| Saturday, December 4, 2010 | 52D | Tony-winning Tessie | Doug Peterson |
| Tuesday, June 8, 2010 | 19A | Milo of "Romeo and Juliet" | Peter A. Collins |
| Wednesday, June 2, 2010 | 33D | Milo of "The Playboys" | Adam Cohen |
| Monday, January 25, 2010 | 31D | Milo of "Ulysses" (3) | Holden Baker |
| Sunday, February 22, 2009 | 50D | Milo of "The Verdict," 1982 (2) | Barry C. Silk & Doug Peterson |
| Thursday, December 25, 2008 | 25D | Dublin-born film star Milo | Eric Tentarelli |
| Wednesday, August 20, 2008 | 27D | Milo of Hollywood | Allan E. Parrish |
| Sunday, March 2, 2008 | 122A | Ice Cube né ___ Jackson | Patrick Blindauer and Tony Orbach |
| Sunday, February 24, 2008 | 82A | Milo of "Ulysses" (3) | Nancy Nicholson Joline |
| Tuesday, July 17, 2007 | 55A | Actor Milo (15) | Natan Last |
| Tuesday, January 16, 2007 | 25D | Actor Milo (15) | Dave Mackey |
| Monday, December 25, 2006 | 22A | Actor Milo (15) | Adam G. Perl |
| Monday, January 9, 2006 | 28D | Actor Milo (15) | Allan E. Parrish |
| Wednesday, December 14, 2005 | 45D | "The Verdict" actor, 1982 | James R. Leeds |
| Tuesday, December 13, 2005 | 39D | Milo of "Barbarella" (3) | Roy Leban |
| Tuesday, September 13, 2005 | 33A | Milo of "Ulysses" (3) | Stella Daily and Bruce Venzke |
| Sunday, April 3, 2005 | 22A | ___ Jackson, a k a Ice Cube | Nancy Nicholson Joline |
| Monday, March 7, 2005 | 12D | Actor Milo (15) | Christina Houlihan Kelly |
| Monday, January 24, 2005 | 15A | Irish-born actor Milo (2) | Sarah Keller |
| Tuesday, December 7, 2004 | 30D | Milo of "Barbarella" (3) | David Diefendorf |
| Wednesday, November 10, 2004 | 16A | Actor Milo (15) | David J. Kahn |
| Sunday, October 3, 2004 | 103D | Milo of "The Verdict," 1982 (2) | Randolph Ross |
| Monday, March 29, 2004 | 6D | Actor Milo (15) | Barry Silk |
| Monday, November 17, 2003 | 54D | Irish-born actor Milo (2) | Sarah Keller |
| Sunday, September 28, 2003 | 55A | Comic actress Tessie (2) | Brendan Emmett Quigley |
| Tuesday, September 2, 2003 | 64A | Actor Milo (15) | Ed Early |
| Wednesday, April 30, 2003 | 2D | Actor Milo (15) | Jerry E. Rosman |
| Sunday, January 26, 2003 | 106D | Milo of "Ulysses," 1967 | Nancy Salomon and Bob Peoples |
| Sunday, August 11, 2002 | 76A | Milo of "Only the Lonely," 1991 | Harvey Estes and Nancy Salomon |
| Wednesday, May 29, 2002 | 4D | Actor Milo (15) | Alan Olschwang |
| Wednesday, November 7, 2001 | 55A | Michael who starred in TV's "It's a Great Life" | Brendan Emmett Quigley |
| Thursday, September 27, 2001 | 26D | Kitty ___ (mistress in Irish history) | Manny Nosowsky |
| Wednesday, June 27, 2001 | 14A | Milo or Tessie (2) | Michael Shteyman |
| Monday, May 28, 2001 | 29D | Milo of "The Verdict" (3) | Gregory E. Paul |
| Tuesday, December 19, 2000 | 8D | Milo of "The Verdict" (3) | Fred Piscop |
| Wednesday, September 20, 2000 | 53D | Actor Milo (15) | Edgar R. Fontaine |
| Saturday, September 11, 1999 | 31D | Comic actress Tessie (2) | Rich Norris |
| Monday, September 6, 1999 | 54D | Actor Milo (15) | Manny Nosowsky |
| Tuesday, June 1, 1999 | 14A | Actor Milo (15) | Myles Callum |
| Tuesday, December 1, 1998 | 48D | Milo or Tessie (2) | Stephanie Spadaccini |
| Monday, October 12, 1998 | 27D | Actor Milo or Michael | Richard Chisholm |
| Tuesday, June 23, 1998 | 48D | Actor Milo (15) | Rich Norris |
| Sunday, May 25, 1997 | 38A | Character actress Tessie | Cathy Millhauser |
| Sunday, April 13, 1997 | 46A | Milo of "Barbarella" (3) | Cathy Millhauser |
| Tuesday, April 8, 1997 | 53D | Actor Milo (15) | Fred Piscop |
| Sunday, December 8, 1996 | 21A | 1982 Tony nominee Milo | A. J. Santora |
| Sunday, January 1, 1995 | 112A | Tony nominee for "Mass Appeal" | Henry Hook |
5 results for OSHEA from older pre-Shortz puzzles.
| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Sunday, May 30, 1993 | 29A | Tessie of music hall fame | A. J. Santora | Maleska |
| Sunday, September 25, 1988 | 112D | Tessie ___, music-hall star | Betty Jorgensen | Maleska |
| Saturday, November 29, 1986 | 30A | Actor Milo | Joe Clonick | Maleska |
| Thursday, September 11, 1986 | 48D | Music-hall star | Charlotte Shore | Maleska |
| Thursday, August 30, 1984 | 25D | Tessie of music-hall fame | Eugene T. Maleska | Maleska |