| Date | Grid | Clue | Author | Editor |
| Wed, Dec 20, 2023 | 50A | N.B.A.'s Westbrook, to fans | Brad Wiegmann | Shortz |
| Wed, May 18, 2022 | 37A | N.B.A. star Westbrook, to fans | Andy Kravis | Shortz |
| Sun, Apr 21, 2019 | 33A | Former Wisconsin senator Feingold | Grant Thackray | Shortz |
| Fri, Apr 15, 2016 | 10D | Bygone sportscaster Hodges | David Steinberg | Shortz |
| Fri, Jan 25, 2013 | 23A | Football Hall-of-Famer Grimm | Joe DiPietro | Shortz |
| Sat, Jun 02, 2012 | 3D | Hodges who called baseball's "shot heard 'round the world" | Tim Croce | Shortz |
| Fri, Aug 19, 2011 | 47D | Former Wisconsin senator Feingold | Patrick Berry | Shortz |
| Thu, Nov 22, 2007 | 24A | Wisconsin senator Feingold | Oliver Hill | Shortz |
| Fri, Feb 03, 2006 | 5D | Sen. Feingold | Manny Nosowsky | Shortz |
| Sat, Dec 11, 2004 | 29D | Sen. Feingold | James E. Buell | Shortz |
| Mon, Dec 22, 2003 | 63A | Old bandleader Columbo | Joy C. Frank | Shortz |
| Sun, Mar 02, 2003 | 33D | Director Meyer | Brendan Emmett Quigley | Shortz |
| Wed, Feb 23, 2000 | 61D | "tom thumb" star Tamblyn | Fred Piscop | Shortz |
| Mon, Sep 13, 1999 | 16A | Moscow's land: Abbr. | Fran and Lou Sabin | Shortz |
| Fri, May 14, 1999 | 21D | Ukr. neighbor | Frank Longo | Shortz |
| Fri, Feb 19, 1999 | 55D | Crooner Columbo | Dana Motley | Shortz |
| Sun, Feb 22, 1998 | 129A | "Tom Thumb" star Tamblyn | Fred Piscop | Shortz |
| Sun, Aug 17, 1997 | 77D | "Tom Thumb" star Tamblyn, 1958 | Cathy Millhauser | Shortz |
| Sun, Mar 23, 1997 | 78A | 30's crooner Columbo | Bryant White | Shortz |
| Sat, Aug 24, 1996 | 38A | Ex-sportscaster Hodges | J. Page | Shortz |
| Sat, May 11, 1996 | 56D | Director Meyer | D. Niles | Shortz |
| Sun, Feb 18, 1996 | 57D | Old bandleader Morgan | Norma Steinberg | Shortz |
| Sat, Feb 10, 1996 | 8D | Wisconsin Senator Feingold | John R. Conrad | Shortz |
| Sun, Jul 02, 1995 | 71A | Bandleader Columbo | Alex K. Justin | Shortz |
| Mon, Dec 13, 1993 | 33D | "Broom Hilda" creator Myers | Thomas W. Schier | Shortz |