| 2026-07-16 | World's most populous Creole-speaking country |
| 2026-07-15 | Island country that's an anagram of TAHITI minus T |
| 2026-06-09 | Western half of Hispaniola |
| 2026-04-19 | Caribbean nation whose name means "land of high mountains" |
| 2026-01-05 | Port-au-Prince's country |
| 2025-08-03 | Major exporter of mangoes |
| 2024-09-26 | Nation to which the island of Tortuga belongs |
| 2024-09-21 | Country with "kreyòl" as an official language |
| 2023-11-26 | Most mountainous Caribbean nation |
| 2023-09-02 | The world's first Black-led republic |
| 2022-09-27 | Most populous Caribbean country |
| 2022-09-19 | About one-third of Hispaniola, area-wise |
| 2021-09-05 | Home of the isle of Tortuga |
| 2020-12-16 | Father of ___ (epithet for Toussaint L'Ouverture) |
| 2019-08-24 | Country whose name anagrams to an island when its fourth letter is doubled |
| 2018-05-08 | Port-au-Prince's land |
| 2018-01-09 | Country to which Frederick Douglass was a U.S. ambassador |
| 2017-03-02 | Country with voodooists |
| 2016-06-29 | Half of Hispaniola |
| 2016-05-03 | Where Toussaint L'Ouverture led a revolt |
| 2016-01-22 | French-speaking land where John James Audubon was born |
| 2015-03-23 | Port-au-Prince's land |
| 2015-02-10 | Port-au-Prince's home |
| 2014-07-25 | Where 18-Downs are currency |
| 2014-05-24 | Recipient of much 2010s humanitarian aid |
| 2014-04-12 | Where Nord, Nord-Est and Nord-Ouest are departments |
| 2013-12-29 | 2010 earthquake site |
| 2013-12-11 | Port-au-Prince's land |
| 2013-03-15 | Big exporter of mangoes |
| 2012-02-07 | Hispaniola's western half |
| 2011-12-24 | Modern-day locale of the place where the Santa Maria ran aground in 1492 |
| 2011-08-01 | French-speaking nation in the Americas |
| 2010-02-21 | Its national anthem is "La Dessalinienne" |
| 2010-01-04 | Jean-Bertrand Aristide's country |
| 2009-12-07 | Country adjacent to the Dominican Republic |
| 2009-07-10 | It has departments named Nord, Sud and Ouest |
| 2008-11-10 | Port-au-Prince's land |
| 2007-04-29 | Country with a palm tree on its flag |
| 2006-11-28 | Half of Hispaniola |
| 2006-01-24 | Half of Hispaniola |
| 2005-07-07 | Land that won its independence in 1804 |
| 2005-06-11 | Site of Toussaint L'Ouverture's revolt |
| 2005-03-31 | Where Columbus made landfall, 1492 |
| 2004-04-26 | Port-au-Prince's land |
| 2004-01-26 | Dominican Republic neighbor |
| 2003-05-03 | Its currency is the gourde |
| 2002-03-31 | Santa Maria wreck site |
| 2001-06-18 | Port-au-Prince is its capital |
| 1999-04-20 | Port-au-Prince's land |
| 1999-04-13 | Papa Doc ruled it |
| 1998-05-17 | Cacao exporter |
| 1998-05-09 | Independent country since 1804 |
| 1998-04-02 | René Préval's domain |
| 1997-09-15 | Port-au-Prince's land |
| 1997-05-25 | Second-oldest country in the Western Hemisphere |
| 1997-05-08 | 1492 Columbus discovery |
| 1996-03-19 | Half of Hispaniola |
| 1995-12-14 | Columbus landfall, 1492 |
| 1994-07-13 | Cole Porter's "Katie Went to _____" |
| 1994-03-06 | Toussaint L'Ouverture's land |