| 2026-04-27 | Chicago slugger |
| 2026-01-24 | One breaking a 108-year drought in 2016 |
| 2025-12-04 | Greenhorn |
| 2025-08-06 | Baby grizzly |
| 2025-03-26 | Baby bear |
| 2024-07-23 | Pup : otter :: ___ : bear |
| 2023-06-15 | Babe in the woods |
| 2023-04-02 | Baby hyena |
| 2023-02-20 | Baby bear |
| 2022-11-15 | Chicago ballplayer |
| 2022-11-11 | Baby cheetah |
| 2022-08-10 | Baby aardvark |
| 2022-06-02 | Ursa minor? |
| 2020-12-21 | Inexperienced reporter |
| 2019-11-09 | Forest newbie |
| 2018-09-30 | N.L. Central player |
| 2017-04-13 | New reporter |
| 2016-05-15 | Predator-to-be |
| 2015-03-23 | Baby bear |
| 2013-06-10 | Wrigley Field player |
| 2013-01-12 | Litter critter |
| 2012-12-11 | Chicago major-leaguer |
| 2012-05-26 | News newbie |
| 2011-07-15 | Den delivery |
| 2010-04-11 | Tiny tiger |
| 2009-03-01 | Kind of reporter |
| 2008-06-21 | See 41-Across |
| 2007-12-05 | One learning the ropes |
| 2005-11-27 | Newbie |
| 2005-09-06 | Wrigley Field player |
| 2005-03-23 | New reporter |
| 2004-02-13 | Pack animal |
| 2003-04-15 | Sammy Sosa, e.g. |
| 2003-03-16 | See 62-Across |
| 2003-02-13 | 62-Across, e.g. |
| 2000-08-29 | Chicago athlete |
| 2000-07-05 | Chicago pro |
| 1999-11-25 | Apprentice |
| 1998-08-25 | Tinker or Evers or Chance |
| 1998-08-03 | Baby bear |
| 1996-07-31 | Babe in the woods |
| 1995-09-14 | Wrigley Field player |
| 1995-01-31 | Wrigley Field player |
| 1994-06-08 | _____ games (Reagan announcing job) |