| 2026-05-17 | Put on the line |
| 2026-03-06 | Consideration in setting insurance rates |
| 2026-01-17 | Cybersecurity assessment |
| 2025-10-12 | Chance |
| 2025-07-30 | Gamble |
| 2024-07-29 | Contest of continental conquest? |
| 2024-05-23 | Dangerous thing to assume |
| 2023-08-12 | Classic board game invented by an Oscar-winning French filmmaker |
| 2023-07-16 | Put on the line |
| 2023-04-02 | War game |
| 2022-10-20 | Flight ___ |
| 2021-09-11 | Take a ___ |
| 2020-12-24 | "The Game of Strategic Conquest" |
| 2019-10-05 | Reward seeker's concern |
| 2019-03-10 | Put at stake |
| 2018-11-11 | Game with 42 territory cards |
| 2018-09-22 | Gamble |
| 2018-04-15 | Word after flight or credit |
| 2017-06-25 | Game played on a map |
| 2017-06-20 | Important consideration for investors |
| 2016-04-13 | Hasbro board game in which armies conquer territories |
| 2016-03-05 | Trusting someone you don't know, e.g. |
| 2016-02-05 | Chance |
| 2014-11-17 | Jeopardize |
| 2014-07-31 | Lender's assessment |
| 2014-06-06 | Decision theory factor |
| 2012-06-09 | Game played across the world |
| 2012-05-23 | Global conquest board game |
| 2010-11-04 | Game played on a world map |
| 2010-08-02 | Hazard |
| 2009-12-18 | Calculated thing |
| 2009-11-02 | Jeopardy |
| 2009-08-25 | Put on the line |
| 2009-07-27 | Jeopardy |
| 2008-05-24 | Gamble |
| 2008-05-04 | Lay on the line |
| 2007-09-08 | Popular U.S. board game since 1959 |
| 2007-03-18 | Underwriter's assessment |
| 2007-01-17 | Classic board game |
| 2006-12-03 | Insurer's calculation |
| 2006-09-11 | Hazard |
| 2006-03-15 | Take a chance |
| 2005-01-15 | Uncertainty |
| 2004-11-20 | It may be calculated |
| 2004-06-15 | Hazard |
| 2003-07-02 | Classic Parker Brothers game |
| 2003-02-09 | Insurer's focus |
| 2003-02-01 | Exposure |
| 2001-10-21 | Daredevil's desire |
| 2001-03-20 | Insurer's calculation |
| 2000-01-21 | Thrill-seeker's love |
| 1999-12-24 | Kind of capital |
| 1999-06-06 | Capitalist's concern |
| 1998-12-02 | Take a chance on |
| 1998-09-25 | Underwriter's concern |
| 1997-05-10 | Put on the line |
| 1996-03-17 | Take a flier |
| 1995-07-20 | Insurance agent's calculation |
| 1994-11-21 | Peril |