| Date | Grid | Clue | Author |
|---|---|---|---|
| Tuesday, June 5, 2012 | 52D | Like some stomachs and elections | Sharon Delorme |
| Sunday, April 22, 2012 | 93A | Breaking sports news, maybe | Paula Gamache and Ed Stein |
| Tuesday, July 19, 2011 | 22D | 16th seed's bracket win, e.g. | Mark Feldman |
| Monday, March 14, 2011 | 4D | Overturn | Andrea Carla Michaels |
| Monday, October 4, 2010 | 64A | Unexpected win | Adam G. Perl |
| Tuesday, February 9, 2010 | 9A | Victory overcoming 100-to-1 odds, e.g. | Robert Cirillo |
| Thursday, June 18, 2009 | 42A | In turmoil (2) | Patrick Blindauer |
| Wednesday, May 27, 2009 | 34A | Dark horse's win | Corey Rubin |
| Thursday, September 25, 2008 | 51D | It's news in sports | Victor Fleming |
| Thursday, May 24, 2007 | 6D | Not happy at all | Patrick Merrell |
| Tuesday, February 6, 2007 | 31D | In a lather | Stella Daily and Bruce Venzke |
| Friday, December 8, 2006 | 46D | Underdog's thrill | Harvey Estes |
| Tuesday, November 28, 2006 | 21A | Underdog's win | Alan Arbesfeld |
| Monday, February 20, 2006 | 43A | Unexpected victory (2) | Doug Peterson |
| Monday, November 14, 2005 | 5A | Unexpected sports outcome (2) | Marjorie Berg |
| Monday, April 11, 2005 | 40D | Unexpected sports outcome (2) | Norma Steinberg |
| Friday, January 21, 2005 | 1D | Surprise at the polls | Frank Longo |
| Sunday, August 3, 2003 | 30D | In turmoil (2) | Jim Page |
| Friday, March 28, 2003 | 48D | Knock down | Cathy Millhauser |
| Monday, June 10, 2002 | 5D | Discombobulate | Sherry O. Blackard |
| Saturday, May 25, 2002 | 61A | Meet surprise | Frank Longo |
| Thursday, January 31, 2002 | 59A | Voters' surprise | Bruce F. Adams |
| Wednesday, October 3, 2001 | 45A | Surprising result | David Bunker |
| Monday, April 2, 2001 | 9A | Unexpected defeat | Peter Gordon |
| Sunday, October 1, 2000 | 80D | Election news (2) | Nancy Nicholson Joline |
| Wednesday, September 6, 2000 | 25A | Underdog's goal | Matt Gaffney |
| Tuesday, March 21, 2000 | 24A | Not happy | Nick Grivas |
| Friday, February 4, 2000 | 48D | Election news (2) | Dana Motley |
| Wednesday, June 2, 1999 | 37D | Having a cow | Nancy Salomon |
| Tuesday, February 23, 1999 | 6D | Discomfit | Robert Zimmerman |
| Tuesday, December 1, 1998 | 60A | Like some stomachs | Stephanie Spadaccini |
| Monday, October 5, 1998 | 46D | Win for the underdog | Peter Gordon |
| Wednesday, August 26, 1998 | 27A | Sports shocker | A. J. Santora |
| Thursday, August 6, 1998 | 30A | Underdog's hope | Fran and Lou Sabin |
| Sunday, August 2, 1998 | 102A | Super Bowl XXXII outcome | Nancy Nicholson Joline |
| Monday, July 13, 1998 | 45D | Come-from-behind victory | Bill Ballard |
| Saturday, September 14, 1996 | 27D | Ruffled | Christopher Page |
| Sunday, May 12, 1996 | 1A | Sports surprise | R. Silvestri |
| Thursday, May 11, 1995 | 38D | Big sports news | Wayne Robert Williams |
| Wednesday, March 8, 1995 | 24A | Unexpected victory (2) | Wayne Robert Williams |
| Sunday, March 5, 1995 | 89D | Disarrange | A.J. Santora |
| Tuesday, July 12, 1994 | 43A | Topple | Charles Arnold |
2 results for UPSET from Variety puzzles.
| Date | Type | Grid | Clue | Author |
|---|---|---|---|---|
| December 11, 2005 | acrostic | F | Underdog's coming-out-on-top | Emily Cox and Henry Rathvon |
| November 18, 2001 | acrostic | X | Stomach problem | Emily Cox and Henry Rathvon |
22 results for UPSET from older pre-Shortz puzzles.
| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Sunday, November 14, 1993 | 114D | Discompose | Norma Steinberg | Taub |
| Sunday, May 30, 1993 | 58A | Troubled | A. J. Santora | Maleska |
| Friday, February 21, 1992 | 43D | Dark horse's potential | Robert Katz | Maleska |
| Sunday, June 30, 1991 | 64D | Capsize | Jacques Liwer | Maleska |
| Friday, August 24, 1990 | 22A | Angry | June A. Boggs | Maleska |
| Wednesday, January 10, 1990 | 47A | Disturbed | Reginald L. Johnson | Maleska |
| Wednesday, August 9, 1989 | 11D | Unnerve | June A. Boggs | Maleska |
| Saturday, May 20, 1989 | 46A | Montclair State beats Notre Dame! | Charles B. Waffell | Maleska |
| Tuesday, April 18, 1989 | 49D | Overturn | Whitten | Maleska |
| Saturday, October 22, 1988 | 26D | Rattled | Jesse Roarke | Maleska |
| Thursday, July 21, 1988 | 52A | Unexpected loss | Eli Wesoff | Maleska |
| Monday, May 25, 1987 | 21D | Surprising victory | Sidney L. Robbins | Maleska |
| Tuesday, January 14, 1986 | 9A | Discomfited | Peter Swift | Maleska |
| Thursday, October 3, 1985 | 45A | Unexpected loss | Eli Wesoff | Maleska |
| Friday, August 30, 1985 | 24A | Tip over | William Canine | Maleska |
| Sunday, April 21, 1985 | 95A | Rattled | Edward Marchese | Maleska |
| Saturday, October 27, 1984 | 59A | Distressed | Peter Swift | Maleska |
| Saturday, March 24, 1984 | 24A | Sports shocker | Hosler | Maleska |
| Sunday, October 30, 1983 | 18A | Sports news | Barry L. Cohen | Maleska |
| Thursday, August 25, 1983 | 41A | The only horse that beat Man o' War | Eli Wesoff | Maleska |
| Wednesday, April 27, 1983 | 29D | Discombobulate | Bert Rosenfield | Maleska |
| Friday, March 4, 1983 | 21A | Disturbed | Ernst Theimer | Maleska |