| 2026-08-26 | ___ Wowie (cocktail with a rhyming name) |
| 2026-06-28 | Home of the Road to Hana, whose 64-mile length contains more than 600 curves |
| 2026-03-31 | Hawaii's second-largest island |
| 2026-03-01 | Popular surfing destination |
| 2026-01-17 | So-called "Valley Isle" |
| 2025-08-25 | Second-largest island in Hawaii |
| 2024-11-03 | Island northwest of the Big Island |
| 2024-04-29 | Closest island to the Big Island |
| 2023-09-24 | Destination for migrating humpback whales |
| 2023-08-09 | Island near the Big Island |
| 2023-03-18 | Trickster in Polynesian mythology |
| 2021-08-31 | Second-largest Hawaiian island |
| 2020-10-05 | Hawaii surfing destination |
| 2020-07-02 | Site of an annual Taro Festival |
| 2020-06-21 | Home to the Hana Highway |
| 2020-06-07 | Island whose name rhymes with 72-Across |
| 2019-07-21 | Second-largest of the Hawaiian Islands |
| 2018-10-09 | Island east of Lanai |
| 2018-07-23 | Island ESE of Oahu |
| 2018-04-09 | Second-largest Hawaiian island |
| 2017-05-29 | Second-largest Hawaiian island |
| 2017-02-27 | Island ESE of Oahu |
| 2016-12-11 | Home of Haleakala National Park |
| 2014-11-02 | Kahakuloa Head locale |
| 2012-11-05 | Island next to Molokai |
| 2012-08-08 | Hawaiian isle |
| 2012-06-06 | Wailuku is its county seat |
| 2012-01-27 | Wailuku's county |
| 2012-01-24 | Site of Haleakala National Park |
| 2011-09-12 | Hawaiian island |
| 2010-08-27 | Lanai's county |
| 2010-03-21 | Where Haiku is |
| 2009-12-13 | Haleakala National Park setting |
| 2009-03-15 | The Pacific's "Valley Isle" |
| 2008-01-21 | Hawaiian island |
| 2007-10-22 | Hawaiian isle |
| 2007-08-27 | Hawaii's "Valley Isle" |
| 2007-06-10 | Windsurfers' mecca |
| 2007-05-08 | Lanai neighbor |
| 2007-03-11 | Neighbor of Lanai |
| 2006-05-08 | Island near Lanai |
| 2005-12-12 | Second-largest of the Hawaiian islands |
| 2005-04-14 | Home of Haleakala National Park |
| 2003-05-14 | Haleakala's locale |
| 2002-05-07 | Part of Hawaii |
| 2002-04-26 | View from Molokai |
| 2001-09-18 | Lanai neighbor |
| 2001-02-11 | Haleakala Crater locale |
| 2001-01-16 | Haleakala National Park site |
| 1998-06-04 | So-called "Valley Isle" |
| 1996-03-21 | Kahului's locale |
| 1994-12-18 | Windsurfers' mecca |