| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Sun, Aug 20, 2023 | 90A | Least inviting | Michael Schlossberg | Shortz |
| Thu, Jan 02, 2020 | 49D | Most bone-chilling | Ed Sessa | Shortz |
| Mon, Dec 09, 2019 | 22A | Most frigid | Ellis Hay | Shortz |
| Sun, Jan 07, 2018 | 108D | Least warm | David Steinberg | Shortz |
| Fri, Dec 26, 2014 | 40A | Most treacherous for driving, maybe | Patrick Berry | Shortz |
| Tue, Dec 21, 2010 | 47A | Least amiable | Alan Arbesfeld | Shortz |
| Sun, Oct 17, 2010 | 51A | Least welcoming | Patrick Blindauer | Shortz |
| Sun, Apr 25, 2010 | 93D | Least friendly | Elizabeth C. Gorski | Shortz |
| Tue, Dec 29, 2009 | 41A | Most dangerous, as winter roads | Peter A. Collins | Shortz |
| Thu, Mar 12, 2009 | 49D | Superlatively slippery | David Chapus | Shortz |
| Fri, Nov 21, 2008 | 18A | Least welcoming | Patrick Berry | Shortz |
| Fri, Jul 25, 2008 | 17A | Least hospitable | John Farmer | Shortz |
| Sun, Nov 26, 2006 | 103D | Least friendly | Manny Nosowsky | Shortz |
| Sun, Nov 19, 2006 | 1A | Most distant | Tony Orbach | Shortz |
| Thu, Jun 24, 2004 | 24D | Most reserved | Patrick Merrell | Shortz |
| Sun, Apr 15, 2001 | 37A | Least emotional | Richard Silvestri | Shortz |
| Sun, Aug 31, 1997 | 6A | Least amiable | David J. Kahn | Shortz |