| 2026-07-02 | Fail to engage |
| 2025-07-01 | Make yawn, say |
| 2024-12-14 | Drip … or drill |
| 2024-09-12 | Tunnel (through) |
| 2024-09-07 | Drill |
| 2024-02-20 | Drill (into) |
| 2023-12-03 | Snooze |
| 2023-09-10 | Snoozefest |
| 2023-04-04 | Make yawn |
| 2023-03-12 | Tedious sort |
| 2022-08-06 | Drip |
| 2021-06-27 | Make yawn |
| 2021-01-09 | Put to sleep |
| 2020-03-23 | Sleep-inducing pill? |
| 2019-11-18 | ___ someone to tears |
| 2019-06-11 | Snoozefest |
| 2019-02-05 | Yawner |
| 2018-02-11 | Induce ennui in |
| 2017-02-23 | Snoozer |
| 2016-06-30 | Gun measure |
| 2016-03-01 | Snoozer |
| 2015-08-29 | Do some drills? |
| 2015-05-20 | Barrel diameter |
| 2015-03-22 | Drill (into) |
| 2014-11-15 | Hollow out |
| 2014-09-12 | "A person who talks when you wish him to listen," per Ambrose Bierce |
| 2014-04-29 | Auger |
| 2014-03-15 | "Zzz" inducer |
| 2013-12-18 | Tiresome sort |
| 2013-07-13 | "Every hero becomes a ___ at last": Emerson |
| 2011-11-14 | Make yawn |
| 2011-09-26 | Drill a hole |
| 2011-02-07 | Snoozefest |
| 2010-04-27 | One who talks only about himself, say |
| 2010-03-22 | Ho-hum sort |
| 2010-02-14 | One who's easier to pray for than to visit, according to C. S. Lewis |
| 2009-11-24 | Droner, usually |
| 2009-02-22 | Put to sleep |
| 2008-08-06 | Drone, e.g. |
| 2007-10-15 | Drill |
| 2007-07-06 | Barrel statistic |
| 2006-10-16 | Bloviator, often |
| 2006-07-27 | Had on one's back |
| 2006-07-03 | Make yawn |
| 2006-05-12 | Drag |
| 2006-03-01 | Ear bender |
| 2005-10-03 | Yawn inducer |
| 2005-09-14 | Yawn producer |
| 2005-05-16 | Make yawn |
| 2004-09-01 | Crashing sort |
| 2004-04-16 | Schmo |
| 2004-02-23 | Wearisome one |
| 2004-01-29 | Drill |
| 2003-05-25 | Yawner |
| 2002-10-16 | Yawner |
| 2002-08-04 | Yielded |
| 2002-03-16 | Put to sleep, maybe |
| 2001-03-13 | Cause to yawn |
| 2001-02-10 | Gun stat |
| 2000-09-03 | Unwanted guest |
| 2000-07-04 | Hardly the life of the party |
| 1998-12-29 | Word with crashing or tidal |
| 1998-10-14 | Use an auger |
| 1998-02-24 | Reduce to tears, maybe |
| 1998-01-09 | Drill |
| 1997-02-14 | Brought forth |
| 1996-10-23 | Crashing type? |
| 1996-10-09 | Drill |
| 1996-06-26 | Barrel diameter |
| 1996-05-07 | Make yawn |
| 1996-03-17 | Drip |
| 1994-08-22 | Yawn inducer |
| 1994-08-05 | Dull fellow |
| 1994-06-03 | Endured |
| 1994-03-20 | Yawn producer |