| 2026-08-31 | Pathetic |
| 2026-06-13 | Pathetic |
| 2026-06-03 | Down in the dumps |
| 2026-04-11 | Disconsolate |
| 2026-03-23 | Bummed out |
| 2026-03-01 | Crestfallen |
| 2026-02-06 | Lachrymose |
| 2026-01-22 | Low |
| 2026-01-14 | Pathetic |
| 2025-11-08 | Unfortunate |
| 2025-07-23 | Disappointing |
| 2025-07-01 | Down |
| 2025-06-19 | "That's very unfortunate" |
| 2025-06-13 | Pitiful |
| 2025-05-08 | Down in the dumps |
| 2025-04-19 | Sorry |
| 2025-04-01 | Down in the dumps |
| 2024-11-05 | Downcast |
| 2024-08-13 | Pathetic |
| 2024-08-07 | Heavy-hearted |
| 2024-08-05 | Forlorn |
| 2024-07-26 | Tearing up, perhaps |
| 2024-05-21 | Down in the dumps |
| 2024-04-24 | Down |
| 2024-04-18 | Heavy-hearted |
| 2024-02-15 | Blue |
| 2024-01-19 | Sorry |
| 2023-12-26 | Disconsolate |
| 2023-12-25 | Unhappy |
| 2023-12-08 | Pitiful |
| 2023-08-29 | In low spirits |
| 2023-08-13 | Down |
| 2023-07-24 | Down in the dumps |
| 2023-07-23 | Sorry |
| 2023-05-08 | Pathetic |
| 2023-03-14 | Down in the dumps |
| 2023-01-26 | Crestfallen |
| 2023-01-03 | Glum |
| 2022-08-28 | Crestfallen |
| 2022-02-03 | Hurl, say |
| 2022-01-13 | Word before case or sack |
| 2021-12-12 | Blue |
| 2021-02-08 | Unhappy |
| 2021-01-26 | Dejected |
| 2020-11-23 | Forlorn |
| 2020-08-22 | In need of a lift? |
| 2020-08-21 | Showing signs of tear? |
| 2020-05-19 | Low-spirited |
| 2020-03-05 | Down in the dumps |
| 2019-12-24 | In need of cheering up |
| 2019-12-23 | "You hate to see it" |
| 2019-12-03 | In a funk |
| 2019-11-15 | Blue |
| 2019-10-08 | Bummed |
| 2019-10-06 | The so-called "winter blues," for short |
| 2019-09-11 | Elegiac |
| 2019-07-15 | Unhappy |
| 2019-06-26 | Down |
| 2019-03-30 | Not up |
| 2019-03-18 | Melancholy |
| 2019-01-31 | Dispirited |
| 2018-10-12 | Bummed |
| 2018-07-15 | Crestfallen |
| 2018-05-12 | Bummed |
| 2018-04-01 | Pathetic |
| 2018-02-28 | Like this emoticon: :-( |
| 2018-02-04 | Regrettable |
| 2018-01-28 | Blue |
| 2018-01-07 | Disappointing |
| 2017-12-28 | End of many a Trump tweet |
| 2017-10-20 | Down |
| 2017-10-12 | Blew |
| 2017-08-21 | Unhappy |
| 2017-07-15 | Deplorable |
| 2017-06-20 | Pitiful |
| 2017-06-16 | Blue |
| 2017-03-11 | Tearing up, say |
| 2017-02-27 | Feeling blue |
| 2017-02-18 | Lame |
| 2016-10-11 | ___ sack |
| 2016-09-29 | Down |
| 2016-09-25 | Down |
| 2016-08-16 | Heartsick |
| 2016-07-22 | Blue |
| 2016-07-10 | In the doldrums |
| 2016-06-13 | Melancholy |
| 2016-05-08 | In a blue state |
| 2016-04-24 | Low |
| 2016-03-05 | Unfortunate |
| 2016-02-03 | Down |
| 2016-01-31 | Blue |
| 2015-11-16 | What this means: :-( |
| 2015-04-09 | Down |
| 2014-12-31 | Pathetic |
| 2014-12-28 | "How pathetic" |
| 2014-11-04 | Down |
| 2014-08-18 | Feeling blue |
| 2014-05-04 | "How ___" |
| 2014-03-05 | Bummed out |
| 2014-02-26 | Like one texting :-( |
| 2014-01-26 | In need of a lift |
| 2013-12-21 | Poor, as an excuse |
| 2013-10-31 | Glum |
| 2013-10-10 | Full of tears, say |
| 2013-08-11 | Plaintive |
| 2013-06-09 | Sorry |
| 2013-05-27 | Glum |
| 2013-04-12 | Out of spirits |
| 2013-04-02 | Unfortunate |
| 2013-01-15 | Melancholy |
| 2012-06-14 | Blue |
| 2012-06-03 | Unfortunate |
| 2012-05-14 | Dispirited |
| 2012-04-16 | Feeling blue |
| 2012-04-08 | What a texter of ":-(" might be |
| 2012-03-21 | Bummed |
| 2011-12-06 | Down |
| 2011-11-29 | Downcast |
| 2011-10-19 | Piteous |
| 2010-11-30 | Bummed out |
| 2010-10-27 | Down |
| 2010-09-06 | Down in the dumps |
| 2010-07-12 | Depressed |
| 2010-07-11 | Down |
| 2010-02-24 | Singing the blues |
| 2010-02-10 | Bummed out |
| 2009-10-07 | Blue |
| 2009-06-13 | Needing buoying |
| 2009-02-13 | Wretched |
| 2008-12-31 | "___ but true" |
| 2008-11-30 | In the dumps |
| 2008-10-15 | Needing a 53-Across |
| 2008-10-01 | Blue |
| 2008-08-26 | Moping |
| 2008-07-22 | Woebegone |
| 2008-07-04 | Blue |
| 2008-05-21 | Inferior, as excuses go |
| 2008-01-27 | Dejected |
| 2007-11-27 | In a funk |
| 2007-11-13 | Bummed out |
| 2007-10-28 | Deplorable |
| 2007-08-24 | Sorry |
| 2007-01-05 | Regrettable |
| 2006-12-27 | Sorry |
| 2006-12-26 | Blue |
| 2006-10-06 | Sorry |
| 2006-09-24 | Blue |
| 2006-09-15 | In need of a lift |
| 2006-07-19 | Bummed |
| 2006-06-03 | Needing a lift |
| 2006-04-15 | Sorry |
| 2005-11-23 | Down |
| 2005-09-26 | Unhappy |
| 2005-08-12 | Sorry |
| 2005-01-13 | Elegiac |
| 2004-11-21 | Depressing |
| 2004-11-07 | Woeful |
| 2004-05-29 | Regrettable |
| 2004-05-20 | Blue |
| 2004-04-21 | Blue |
| 2004-03-21 | Down |
| 2004-02-22 | "Mr. Dieingly ___" (1966 Critters hit) |
| 2003-07-06 | Sorry |
| 2003-06-29 | Blue |
| 2003-05-28 | In a blue funk |
| 2003-05-27 | Dejected |
| 2003-01-03 | Down |
| 2002-12-19 | Blue |
| 2002-12-01 | Sorry |
| 2002-08-11 | Blue |
| 2002-05-31 | Low |
| 2002-03-08 | Like some commentary |
| 2001-09-10 | Jerry Lewis movie "The ___ Sack" |
| 2001-05-16 | Down in the dumps |
| 2001-02-28 | Bummed |
| 2000-12-21 | Woebegone |
| 2000-11-12 | Kind of story |
| 2000-11-01 | In the doldrums |
| 2000-08-09 | Frowning |
| 2000-08-06 | Regrettable |
| 2000-05-10 | Blue |
| 2000-04-11 | In a funk |
| 2000-02-29 | Blue |
| 2000-02-08 | In a funk |
| 1999-12-25 | Down |
| 1999-11-21 | Down |
| 1999-09-24 | Blue |
| 1999-09-01 | Dispirited |
| 1999-08-31 | Bummed out |
| 1999-06-02 | Regrettable |
| 1999-04-18 | Melancholy |
| 1999-02-04 | Insufficient, as an excuse |
| 1998-12-03 | Blue |
| 1998-11-26 | Unfortunate |
| 1998-11-21 | Regrettable |
| 1998-10-11 | Deplorably poor |
| 1998-06-02 | Frowning |
| 1998-04-08 | Singing the blues |
| 1998-03-23 | In low spirits |
| 1998-01-25 | Down |
| 1997-12-31 | Woeful |
| 1997-12-18 | Long-faced |
| 1997-09-28 | Deplorable |
| 1997-08-19 | Down |
| 1997-06-29 | Lugubrious |
| 1997-06-08 | Down |
| 1997-06-05 | Blue |
| 1997-03-16 | Blue |
| 1997-03-15 | Not up |
| 1997-03-06 | Down |
| 1996-11-08 | Glum |
| 1996-08-02 | Pitiful |
| 1996-06-04 | Down |
| 1996-04-03 | Pathetic |
| 1996-03-17 | Blue |
| 1995-11-26 | Heartsick |
| 1995-10-15 | Pathetic |
| 1995-07-21 | Pathetic |
| 1995-07-14 | Inferior, as an excuse |
| 1995-04-15 | Crushed |
| 1995-04-03 | Blue |
| 1995-02-11 | Sorry |
| 1995-01-24 | In low spirits |
| 1995-01-23 | Despondent |
| 1994-12-29 | Long-faced |
| 1994-09-04 | Blue |
| 1994-09-02 | Down, so to speak |
| 1994-08-16 | Forlorn |
| 1994-08-03 | Plaintive |
| 1994-06-26 | Kind of sack |
| 1994-05-01 | Lugubrious |
| 1994-04-13 | Rueful |
| 1994-03-13 | Like McCuller's cafe |
| 1994-02-04 | Downcast |
| 1994-01-30 | Triste |