| 2026-04-12 | Starting point of Diana Nyad's 2013 swim to Florida |
| 2025-04-22 | Island north of Jamaica |
| 2024-05-26 | Island country sometimes called "El Cocodrilo" for its shape |
| 2024-04-16 | Starting point for a record-setting swim in 2023's "Nyad" |
| 2023-03-25 | Home to the world's smallest bird, the bee hummingbird, which measures just 2.25" |
| 2023-03-12 | Hemingway's home for over 20 years |
| 2023-01-19 | Isla de la Juventud locale |
| 2022-10-24 | Actor Gooding Jr. |
| 2022-03-21 | Havana is its capital |
| 2021-12-09 | Home of the 62-Down hummingbird, the world's smallest bird |
| 2020-08-10 | Bay of Pigs locale |
| 2020-04-22 | Home to the Bay of Pigs |
| 2020-04-06 | Havana's home |
| 2019-08-12 | Havana's home |
| 2019-08-04 | Olympic powerhouse in boxing |
| 2019-02-27 | Target of the U.S.-backed Radio Martí |
| 2018-05-20 | Where Hemingway wrote "The Old Man and the Sea" |
| 2017-05-05 | 1962 Organization of American States expellee |
| 2017-02-14 | Country with which the U.S. re-established diplomatic relations in 2015 |
| 2017-01-11 | Historic 2016 Obama destination |
| 2015-12-01 | Guantánamo Bay locale |
| 2015-03-04 | Homeland of many Miamians |
| 2014-08-15 | Island sometimes called El Cocodrilo |
| 2014-07-27 | Country with the most all-time medals in Olympic baseball |
| 2013-07-06 | Home to Morro Castle |
| 2012-09-30 | 1950s coup site |
| 2012-01-24 | Locale of Guantánamo Bay |
| 2010-08-24 | Destination of many 1960s-'70s airplane hijackings |
| 2008-08-10 | International baseball powerhouse |
| 2008-01-08 | Bay of Pigs locale |
| 2006-04-24 | It's south of Florida |
| 2003-07-30 | San Juan Hill site |
| 2003-05-05 | Castro's country |
| 2003-04-28 | Havana's home |
| 2002-03-14 | Embargoed land |
| 2001-12-18 | Bay of Pigs location |
| 2001-10-29 | Where many Miamians were born |
| 2001-09-28 | Santiago de ___ |
| 2000-03-02 | Embargoed country |
| 1996-05-01 | Home of 49-Across |
| 1994-09-01 | Sierra Maestra country |
| 1994-05-15 | Where the conga originated |
| 1993-12-28 | Actor Gooding |