| #8595, aired 2022-03-11 | 6-LETTER WORLD CAPITALS $1600: Known as the "City of Columns", it's one of the oldest in the Caribbean Havana |
| #8467, aired 2021-09-14 | CENTRAL AMERICAN CAPITALS $1200: Belmopan, with a population about the capacity of Madison Square Garden, is the capital of this nation on the Caribbean Belize |
| #7883, aired 2018-12-12 | WORLD CAPITALS $800: In 1749 the French laid out this Caribbean capital in a grid pattern & called it L'Hopital Port-au-Prince |
| #7762, aired 2018-05-15 | WORLD CAPITALS $2,500 (Daily Double): You need to use 2 hyphens when spelling the name of this Caribbean capital founded in 1749 Port-au-Prince |
| #7135, aired 2015-09-25 | SOUTH AMERICAN CAPITALS $600: Oils well that ends well in this city by the Caribbean coast that became a capital in the 1820s Caracas |
| #6560, aired 2013-03-08 | CARIBBEAN CAPITALS $400: Spice baskets are popular gift items you can purchase in St. George's, capital of this island invaded by the U.S. in 1983 Grenada |
| #6560, aired 2013-03-08 | CARIBBEAN CAPITALS $800: (I'm Anderson Cooper.) The morning after a catastrophic earthquake rocked Haiti, I, as the first American journalist on the ground, broadcast the devastation of this capital Port Au Prince |
| #6560, aired 2013-03-08 | CARIBBEAN CAPITALS $1200: H.M. [Her Majesty's] Prison, which dates to the 1840s, is the oldest building in Road Town, the capital of this British island group the British Virgin Islands |
| #6560, aired 2013-03-08 | CARIBBEAN CAPITALS $1600: This capital of Antigua & Barbuda shares its name with the capital of Newfoundland St. John's |
| #6560, aired 2013-03-08 | CARIBBEAN CAPITALS $2000: Trinidad & Tobago's capital has this name; sounds like Barcelona or someplace Port of Spain |
| #6309, aired 2012-02-09 | WORLD CAPITALS $1200: The Plaza de la Revolucion in this Caribbean capital was often the site of revolutionary speeches, including a 7-hour one Havana |
| #5797, aired 2009-11-24 | WORLD CAPITALS $1200: It's the largest English-speaking city in the Caribbean, mon Kingston (Jamaica) |
| #5264, aired 2007-06-28 | CAPITALS OF THE WEST INDIES $200: A narrow peninsula called the Palisados protects this Jamaican port from the Caribbean Sea Kingston |
| #5204, aired 2007-04-05 | WORLD CAPITALS $400: A Caribbean nation: Santo Domingo Dominican Republic |
| #4091, aired 2002-05-20 | SOUTH AMERICAN CAPITALS $1600: La Guaira is its Caribbean sea port Caracas |
| #3402, aired 1999-05-25 | WORLD CAPITALS $2,000 (Daily Double): From 1936 to 1961 this Caribbean capital was known as Ciudad Trujillo in honor of dictator Rafael Trujillo Santo Domingo |
| #3083, aired 1998-01-14 | CARIBBEAN CAPITALS $100: You can see some of Pablo Casals' favorite cellos at the museum devoted to him in this Puerto Rican capital San Juan |
| #3083, aired 1998-01-14 | CARIBBEAN CAPITALS $200: Spice baskets are popular souvenirs of St. George's, the capital of this country invaded by the U.S. in 1983 Grenada |
| #3083, aired 1998-01-14 | CARIBBEAN CAPITALS $300: Road Town is not only the capital but the only urban area in this British island group British Virgin Islands |
| #3083, aired 1998-01-14 | CARIBBEAN CAPITALS $400: Dance lovers know there's an annual merengue festival in this capital of the Dominican Republic Santo Domingo |
| #3083, aired 1998-01-14 | CARIBBEAN CAPITALS $500: Willemstad, the capital of Curacao, has an 18th century fort named for this European capital Amsterdam |
| #1887, aired 1992-11-17 | WORLD CAPITALS $400: This South American capital lies only 7 miles inland from the Caribbean Sea Caracas, Venezuela |
| #1428, aired 1990-11-14 | WORLD CAPITALS $1000: This Caribbean capital lies near the foothills of the Blue Mountains Kingston (Jamaica) |
| #1372, aired 1990-07-17 | WORLD CAPITALS $600: The capitals of Newfoundland & the Caribbean country of Antigua & Barbuda share this name St. John's |
