| Date | Grid | Clue | Author | Editor |
| Mon, Aug 28, 2023 | 67A | Like wingtips and penny loafers | Brian Callahan | Shortz |
| Fri, Oct 08, 2021 | 40A | Cry heard at a shoe auction? | Yacob Yonas | Shortz |
| Wed, May 06, 2020 | 31D | Like shoes | Ali Gascoigne | Shortz |
| Sat, Mar 23, 2019 | 29D | Leather-___ shoes | David Steinberg | Shortz |
| Sun, Jul 09, 2017 | 22A | Like boots | Will Nediger | Shortz |
| Sun, May 14, 2017 | 40A | Did a cobbler's job on | Will Nediger | Shortz |
| Thu, Feb 16, 2017 | 67A | Thick-___ shoes | Keith Redwine | Shortz |
| Sun, May 08, 2016 | 59D | Like clogs, say | David J. Kahn | Shortz |
| Thu, Mar 10, 2016 | 27D | Did a cobbler's job on | Ed Sessa | Shortz |
| Fri, Aug 03, 2012 | 52D | Rubber-___ | Jeff Chen | Shortz |
| Sun, May 06, 2012 | 73D | Like a shoe | Alex Vratsanos | Shortz |
| Sun, Jan 25, 2009 | 38D | Having a bottom | Michael Torch | Shortz |
| Thu, Feb 22, 2007 | 42A | Having a bottom | Mike Nothnagel | Shortz |
| Sun, Nov 14, 2004 | 101D | Did a cobbler's job | Harvey Estes and Nancy Salomon | Shortz |
| Sun, Aug 25, 2002 | 43D | Having a bottom | Randolph Ross | Shortz |
| Sun, Sep 02, 2001 | 102D | Like pumps | Manny Nosowsky | Shortz |
| Wed, Apr 01, 1998 | 41A | Like a shoe | Alan Arbesfeld | Shortz |
| Sun, Dec 01, 1996 | 19A | Like a shoe | D. J. Kahn | Shortz |
| Sun, Aug 25, 1996 | 31A | Worked on pumps | R. Silvestri | Shortz |
| Sun, Mar 24, 1996 | 40A | Like shoes | J. K. Brill | Shortz |
| Sat, Dec 30, 1995 | 47D | Put bottoms on | Joe DiPietro | Shortz |
| Mon, Jul 31, 1995 | 61A | Like oxfords | Elizabeth Gorski | Shortz |
| Mon, Apr 24, 1995 | 46D | Like shoes | Sidney L. Robbins | Shortz |
| Tue, Oct 11, 1994 | 71A | Did a cobbler's job | Bernice Gordon | Shortz |
| Thu, Sep 29, 1994 | 32D | Cobbled | Randolph Ross | Shortz |