| Date | Grid | Clue | Author | Editor |
| Fri, Mar 01, 2019 | 39D | Island in the West Indies | Zhouqin Burnikel | Shortz |
| Sat, Nov 04, 2017 | 32A | Island on which Mount Obama is the highest point | Michael Shteyman | Shortz |
| Wed, Dec 14, 2011 | 5D | Barbuda's island partner | Tim Croce | Shortz |
| Sat, Jun 25, 2011 | 10D | St. John's is its capital | Barry C. Silk | Shortz |
| Wed, Mar 25, 2009 | 47A | One of the Leeward Islands | Jerry E. Rosman | Shortz |
| Sat, Oct 01, 2005 | 3D | West Indies island | Joe DiPietro | Shortz |
| Sat, Aug 24, 2002 | 2D | Its leading city is St. John's | Chuck Menning | Shortz |
| Fri, Jul 10, 1998 | 25D | Island Columbus reached in 1493 | Brendan Emmett Quigley | Shortz |
| Sun, Mar 16, 1997 | 17D | 1493 Columbus landing site | David J. Kahn | Shortz |
| Sun, Dec 29, 1996 | 3D | One of the Leeward Islands | B. White | Shortz |
| Sat, Oct 26, 1996 | 15A | Columbus discovery of 1493 | D. Niles | Shortz |