| 2026-05-08 | Second City district, with "the" |
| 2024-09-17 | Prominent part of a bowline knot |
| 2024-08-02 | Drum machine creation |
| 2024-06-10 | "Bunny ear" made while tying a shoelace |
| 2024-04-26 | Keep informed, with "in" |
| 2023-12-31 | Bring (in) |
| 2023-08-11 | Play on repeat |
| 2023-04-11 | Roller coaster feature |
| 2021-11-21 | In the ___ |
| 2020-10-11 | Aerial maneuver |
| 2020-04-20 | Circle |
| 2018-06-20 | Repeating segment of computer code |
| 2017-05-06 | Circuit |
| 2016-07-14 | Air show maneuver |
| 2015-09-24 | Aerial stunt |
| 2015-07-26 | Tax dodger's discovery |
| 2014-09-18 | Airport shuttle route, commonly |
| 2014-02-03 | Circle |
| 2014-01-21 | See 1-Across |
| 2013-12-01 | - |
| 2013-11-17 | Lariat part |
| 2013-10-11 | Ring |
| 2013-10-05 | 1 Infinite ___ (address of Apple's headquarters) |
| 2013-04-15 | Circle |
| 2012-01-31 | Stunt plane maneuver |
| 2011-12-15 | Word with belt or tape |
| 2011-12-04 | Möbius strip, e.g. |
| 2011-09-12 | Encircle |
| 2011-03-29 | Heart of Chicago, with "the" |
| 2010-12-12 | Coil |
| 2010-09-13 | Part of a shoelace tie |
| 2009-12-06 | Ankh's top |
| 2008-08-27 | In the ___ |
| 2008-08-19 | Chicago district, with "the" |
| 2007-11-25 | Figure skating maneuver |
| 2007-07-29 | Circle |
| 2007-01-14 | Ankh feature |
| 2006-10-12 | Bow part |
| 2006-07-16 | Flight maneuver |
| 2005-06-06 | Part of a tied tie |
| 2004-08-09 | Circle |
| 2004-07-11 | What goes around |
| 2003-10-06 | Chicago locale, with "the" |
| 2003-08-25 | Orbit |
| 2001-09-08 | Ankh feature |
| 2000-10-24 | Aerial maneuver |
| 2000-07-04 | Roller coaster part |
| 2000-06-27 | Cloverleaf feature |
| 1999-07-23 | Computer program feature |
| 1999-06-01 | Roller coaster maneuver |
| 1998-07-26 | Continuous-play tape |
| 1996-10-21 | Aeronautical maneuver |
| 1996-01-29 | Aerobatic maneuver |
| 1995-05-05 | In the _____ (informed) |
| 1995-03-15 | Chicago area, with "the" |
| 1994-12-09 | Enwreathe |