| 2026-06-25 | Minor municipality |
| 2025-06-07 | Gown go-with |
| 2024-06-17 | Unit of suburbia |
| 2022-11-27 | Hamlet's cousin |
| 2021-02-28 | You might skip it if you're in trouble |
| 2020-04-05 | "Old ___ Road," longest-running #1 single in Billboard history (19 weeks) |
| 2019-07-25 | Flee to avoid obligations, say |
| 2019-05-19 | Word with boom or skip |
| 2018-04-29 | Burg |
| 2016-11-15 | "My Kind of ___ (Chicago Is)" |
| 2016-08-03 | Hamlet's relative |
| 2015-05-18 | Village |
| 2014-06-18 | Mini-metro |
| 2013-08-28 | Go to ___ on |
| 2013-07-03 | Ending with George or James |
| 2012-07-09 | Village |
| 2011-12-02 | Hamlet's cousin |
| 2011-05-10 | Burg |
| 2011-03-23 | It may have a square in the middle |
| 2006-12-20 | Burg |
| 2005-11-23 | Crier's place |
| 2005-11-04 | Hamlet's big brother |
| 2005-09-26 | See 2-Down |
| 2005-05-10 | See 10-Across |
| 2005-05-05 | See 38-Across |
| 2005-03-27 | Something painted red |
| 2004-12-26 | Country partner? |
| 2004-04-28 | It may be painted red |
| 2003-07-20 | Word with ghost or boom |
| 2003-05-18 | Out of ___ (away) |
| 2001-09-22 | Podunk, e.g. |
| 2001-05-24 | Square setting |
| 2000-11-28 | Burg |
| 2000-01-20 | Hamlet's cousin |
| 1999-01-10 | Word before house or hall |
| 1998-07-03 | Kind of hall |
| 1997-10-15 | Atlas dot |
| 1996-10-24 | Borough |
| 1996-08-13 | Burg |
| 1995-09-07 | Hamlet |
| 1995-04-27 | Word with China or ghost |
| 1995-03-13 | Burg |
| 1994-12-18 | Shute's "A _____ Like Alice" |
| 1994-12-02 | Burg |