| Date | Grid | Clue | Author | Editor |
| Fri, Aug 07, 2020 | 32D | Poet whose name consists of side-by-side opposites | Tom Pepper | Shortz |
| Tue, Jul 09, 2019 | 35A | "The Highwayman" poet | Bruce Haight | Shortz |
| Sun, Nov 27, 2016 | 50D | "The Highwayman" poet | Matt Ginsberg | Shortz |
| Thu, Nov 19, 2015 | 47D | Alfred who wrote "The Highwayman" | Andrew Zhou | Shortz |
| Wed, Mar 13, 2013 | 13D | Poet best known for "The Highwayman" | Joe DiPietro | Shortz |
| Tue, Jul 17, 2012 | 40D | "The Highwayman" poet | Peter A. Collins | Shortz |
| Sun, Apr 29, 2007 | 32A | Poet with a seemingly self-contradictory name | Henry Hook | Shortz |
| Wed, Apr 26, 2006 | 57D | "The Highwayman" poet | Stella Daily and Bruce Venzke | Shortz |
| Tue, Aug 03, 2004 | 48D | "The Highwayman" poet Alfred | Roy Leban | Shortz |
| Sun, May 12, 1996 | 87D | "The Highwayman" poet | R. Silvestri | Shortz |
| Sat, Apr 01, 1995 | 69A | "The Highwayman" penner | Fred Piscop | Shortz |
| Sun, Mar 05, 1995 | 115A | "The Barrel-Organ" poet | A.J. Santora | Shortz |
| Tue, Dec 13, 1994 | 13D | Poet Alfred | Jon Delfin | Shortz |
| Sun, Nov 28, 1993 | 68A | "The Highwayman" poet | Joanne W. Edwards | Shortz |