| 2026-08-04 | Word aptly hidden in "moldy" |
| 2026-06-14 | Totally played out |
| 2026-06-01 | Dated |
| 2026-05-21 | Like news that everyone already knows |
| 2026-02-06 | Played out |
| 2026-01-16 | It takes a long time to get this |
| 2026-01-05 | Passé |
| 2025-12-09 | Historical |
| 2025-11-27 | Like nonagenarians |
| 2025-11-21 | Senescent |
| 2025-11-17 | Like a centenarian |
| 2025-07-22 | Obsolete |
| 2025-07-03 | Like well-known news |
| 2025-05-05 | Up there in years |
| 2025-03-25 | Obsolete |
| 2025-02-27 | Previous |
| 2025-01-08 | Word with style or fashioned |
| 2024-12-18 | Not funny anymore |
| 2024-12-09 | Passé |
| 2024-11-06 | Like food you should probably smell before eating |
| 2024-10-16 | Well-worn |
| 2024-10-01 | Like Father Time |
| 2024-08-28 | Up there, so to speak |
| 2024-08-25 | Antediluvian |
| 2024-07-09 | Worn, maybe |
| 2024-06-13 | Like Saint Nick |
| 2024-02-12 | What a good joke never gets |
| 2024-02-08 | Well-seasoned |
| 2023-12-19 | Shabby, maybe |
| 2023-12-10 | Tired |
| 2023-09-13 | No longer in use |
| 2023-09-12 | ___-fashioned (cocktail) |
| 2023-05-14 | Longtime |
| 2023-03-09 | Played out |
| 2023-01-23 | Aged |
| 2022-08-23 | Word before or after age |
| 2022-05-20 | Up there, you might say |
| 2022-05-01 | No longer funny |
| 2022-04-25 | Grayed |
| 2022-04-13 | Stale |
| 2022-03-01 | *___ Square (translation of "Vieux Carré") |
| 2021-11-08 | ___ Man Winter |
| 2021-10-16 | Discontinued |
| 2021-05-05 | Antique |
| 2021-03-17 | Like Mother Hubbard and King Cole |
| 2021-01-20 | Bygone |
| 2020-12-22 | Aged |
| 2020-12-08 | Like the year you ring out on December 31 |
| 2020-09-02 | Stale |
| 2020-05-03 | Lacking originality |
| 2020-04-23 | What it takes years and years to grow |
| 2020-02-17 | With 33-Down, the U.S. flag, affectionately |
| 2019-11-13 | In disuse |
| 2019-10-21 | Longtime |
| 2019-10-07 | Outdated |
| 2019-09-10 | Like 1960s-'70s music |
| 2019-08-17 | Hackneyed |
| 2019-07-23 | Timeworn |
| 2019-06-12 | Antiquated |
| 2019-06-06 | Discontinued |
| 2019-06-02 | Part of V.S.O.P. |
| 2019-04-04 | What one gets after many years of work |
| 2019-03-26 | Like Mother Hubbard |
| 2019-03-01 | Hackneyed |
| 2018-12-29 | Up there, so to speak |
| 2018-09-11 | Long in the tooth |
| 2018-07-11 | Up there in years |
| 2018-06-03 | Dated |
| 2018-05-28 | Antiquated |
| 2018-05-07 | Ancient |
| 2018-05-06 | Smelling of mothballs |
| 2018-02-23 | Dated |
| 2017-12-24 | ___ Father Christmas |
| 2017-10-23 | So last year |
| 2017-08-10 | Hoary |
| 2017-06-12 | Outdated |
| 2017-05-22 | Not new |
| 2017-05-08 | Superannuated |
| 2017-05-04 | White-haired |
| 2017-03-30 | What it takes decades to grow |
| 2017-02-19 | Trite |
| 2016-12-19 | Right jolly ___ elf (Santa) |
| 2016-11-16 | Like most knock-knock jokes |
| 2016-09-18 | So last month |
| 2016-08-01 | Aged |
| 2016-06-06 | Long in the tooth |
| 2016-05-05 | Dated |
| 2016-04-01 | "___ New Hampshire" (state song) |
| 2016-03-20 | Up in years |
| 2015-11-08 | Like a chestnut |
| 2015-09-07 | Passé |
| 2015-08-09 | Onetime |
| 2015-05-25 | Like Mother Hubbard |
| 2015-05-01 | White-haired |
| 2015-03-26 | Onetime |
| 2015-03-11 | No longer funny |
| 2015-02-22 | Getting on |
| 2014-10-19 | Discontinued |
| 2014-06-20 | See 29-Across |
| 2014-06-10 | Superannuated |
| 2014-03-06 | Familiar |
| 2013-12-01 | Superseded |
| 2013-10-10 | Traditional |
| 2013-09-02 | Aged |
| 2013-06-23 | Over the hill |
| 2013-05-14 | Antiquated |
| 2013-04-28 | Seasoned |
| 2013-01-23 | Not funny anymore |
| 2012-12-30 | Timeworn |
| 2012-12-29 | Played out |
| 2012-11-19 | Long in the tooth |
| 2012-11-15 | Outdated |
| 2012-09-28 | Like chestnuts |
| 2012-05-29 | Bygone |
| 2012-05-10 | Erstwhile |
| 2012-04-08 | ___ school |
| 2012-04-06 | Bygone |
| 2012-03-05 | Obsolete |
| 2011-11-07 | Superannuated |
| 2011-08-22 | Superannuated |
| 2011-07-21 | See 27-Down |
| 2011-07-05 | Like Mother Hubbard |
| 2011-05-05 | No longer used |
| 2011-03-15 | So last year |
| 2011-03-02 | Archaic |
| 2011-03-01 | Long in the tooth |
| 2011-01-09 | Outdated |
| 2010-12-11 | 19th-century, say |
| 2009-12-22 | Jolly ___ Saint Nick |
| 2009-09-14 | Antiquated |
| 2009-05-31 | Primeval |
| 2009-05-23 | With 41-Across, one you go way back with |
| 2008-09-24 | Out of vogue |
| 2008-07-10 | Past |
| 2008-07-03 | With 19-Across, language from which "steak" and "eggs" come |
| 2008-02-04 | Outdated |
| 2008-01-01 | Superannuated |
| 2007-09-11 | Like Methuselah |
| 2007-06-21 | Moth-eaten |
| 2007-05-01 | Former |
| 2007-03-13 | Bygone |
| 2007-01-17 | Familiar |
| 2006-12-25 | Passé |
| 2006-12-04 | Getting on in years |
| 2006-10-02 | Going way back, as friends |
| 2006-06-28 | Antiquated |
| 2006-06-22 | Getting tiresome |
| 2006-05-22 | No longer funny |
| 2006-02-26 | Outworn |
| 2006-01-18 | Antediluvian |
| 2005-12-29 | Like the hills |
| 2005-10-19 | Not fresh |
| 2005-09-28 | Moth-eaten |
| 2005-09-26 | The "O" in G.O.P. |
| 2005-09-25 | Outmoded |
| 2005-08-21 | Fossilized |
| 2005-06-12 | Past |
| 2005-05-21 | Familiar |
| 2005-02-13 | See 51-Down |
| 2004-12-19 | Hoary |
| 2004-12-07 | Moth-eaten |
| 2004-11-22 | Prehistoric |
| 2004-11-14 | Stale |
| 2004-11-11 | Time-worn |
| 2004-09-20 | Discontinued |
| 2004-09-13 | Bygone |
| 2004-06-29 | Moth-eaten |
| 2004-06-21 | Outdated |
| 2004-06-06 | Stale |
| 2004-05-17 | Aged |
| 2004-04-19 | On in years |
| 2004-02-19 | Used |
| 2004-01-04 | 80-Across, in English |
| 2003-11-09 | Not cutting-edge |
| 2003-10-30 | Erstwhile |
| 2003-10-21 | Like the farmer MacDonald |
| 2003-05-04 | Not funny anymore |
| 2003-04-27 | Something ___ (bride's need) |
| 2003-03-11 | Timeworn |
| 2002-11-28 | Prehistoric |
| 2002-10-02 | OPPOSITE OF 11-DOWN |
| 2002-05-16 | Dated |
| 2002-04-18 | 80 or over, say |
| 2002-04-14 | Prehistoric |
| 2002-01-21 | Aged |
| 2001-11-03 | Follower or preceder of age |
| 2001-10-26 | Timeworn |
| 2001-09-26 | With 58-Down, Civil War battle eagle named after the president |
| 2001-09-19 | Antique |
| 2001-08-19 | Fossillike |
| 2001-08-09 | Word before school or master |
| 2001-06-10 | ___ Navy |
| 2001-04-23 | With 42-Down, out-of-date |
| 2001-04-16 | Like octogenarians |
| 2001-04-06 | Gray, say |
| 2000-12-18 | Up there in years |
| 2000-11-30 | Out of production |
| 2000-10-16 | Worn out |
| 2000-10-08 | Medieval |
| 2000-08-26 | With 34-Down, bygone Baltic language |
| 2000-08-15 | Vintage |
| 2000-07-16 | With 44-Across, a veteran |
| 2000-07-12 | Getting on |
| 2000-05-05 | Unmodernized |
| 2000-05-04 | Previously heard |
| 2000-04-17 | Elderly |
| 2000-04-09 | From an earlier time |
| 2000-02-13 | Passé |
| 1999-11-18 | Word with hand or hat |
| 1999-08-11 | Ancient |
| 1999-07-27 | Gone gray, say |
| 1999-06-15 | Archaic |
| 1999-06-05 | Experienced, as a pro |
| 1998-12-27 | Much-used |
| 1998-11-14 | Worn |
| 1998-09-07 | Long in the tooth |
| 1998-07-26 | Vintage |
| 1998-04-19 | Hackneyed |
| 1998-02-03 | Getting on in years |
| 1997-11-29 | Dated |
| 1997-09-29 | Elderly |
| 1997-09-23 | Like the gray mare |
| 1997-09-04 | Part of O.T. |
| 1997-06-17 | Aged |
| 1997-05-13 | Like a centenarian |
| 1996-11-05 | Superannuated |
| 1996-09-26 | On in years |
| 1996-08-20 | Aged |
| 1996-07-16 | Like grandpa |
| 1996-02-24 | Getting on |
| 1995-10-22 | _____ guard |
| 1995-10-01 | Immemorial |
| 1995-09-06 | Methuselah-like |
| 1995-05-25 | Familiar |
| 1995-05-17 | Outmoded |
| 1995-04-10 | _____ Glory |
| 1995-02-17 | Time-worn |
| 1994-12-22 | Pre-Columbian |
| 1994-12-21 | Used |
| 1994-12-19 | Vintage |
| 1994-08-20 | Requiring many candles |
| 1994-07-19 | Getting on |
| 1994-07-05 | Timeworn |
| 1994-06-26 | Well-worn |
| 1994-06-10 | Former |
| 1994-02-05 | Mossy |
| 1993-12-30 | Twice-told |