| Date | Grid | Clue | Author | Editor |
| Fri, May 05, 2023 | 43A | Leeward island where Alexander Hamilton was born | Jacob McDermott | Shortz |
| Sat, Jun 26, 2021 | 7D | Tropical island whose name comes from the Spanish for "snows" | John Lieb and Brad Wilber | Shortz |
| Tue, Feb 04, 2020 | 51A | St. Kitts's island partner | Queena Mewers and Alex Eaton-Salners | Shortz |
| Sat, May 11, 2019 | 37A | Neighbor of 5-Down | Robyn Weintraub | Shortz |
| Fri, Aug 29, 2014 | 27A | Neighbor of St. Kitts | Daniel Raymon | Shortz |
| Wed, Sep 14, 2011 | 40A | Neighbor of St. Kitts | Jeff Chen | Shortz |
| Sat, Feb 18, 2006 | 20D | One of the Leeward Islands | Eric Berlin | Shortz |
| Wed, Feb 01, 2006 | 1D | English-speaking Caribbean island | Elizabeth C. Gorski | Shortz |
| Mon, Mar 29, 1999 | 19A | St. Kitts and ___ (Caribbean nation) | Bill Ballard | Shortz |
| Thu, Oct 05, 1995 | 14D | Island near St. Kitts | Christopher Page | Shortz |