| Date | Grid | Clue | Author | Editor |
| Wed, Mar 13, 2024 | 67A | Amount at stake | Drew Schmenner | Shortz |
| Thu, Jun 04, 2020 | 26D | Speculate | Barbara Lin | Shortz |
| Tue, Jun 11, 2019 | 51D | Bet | David J. Kahn | Shortz |
| Fri, Mar 03, 2017 | 46D | Bucks on a horse, e.g. | Patrick Berry | Shortz |
| Tue, Jan 25, 2011 | 26D | "Friendly" action | Randall J. Hartman | Shortz |
| Mon, Jun 07, 2010 | 6D | Transaction at a racetrack | Lynn Lempel | Shortz |
| Tue, Aug 11, 2009 | 64A | $2 on the gray mare, e.g. | Oliver Hill | Shortz |
| Wed, Aug 08, 2007 | 51D | It might be placed at a window | Donna S. Levin | Shortz |
| Sat, Jun 02, 2007 | 35A | Something often laid at a window | Byron Walden | Shortz |
| Thu, May 29, 2003 | 58A | Two chips, perhaps | Jim Page | Shortz |
| Wed, Jun 14, 2000 | 40A | Stake | Nancy Salomon and Sherry O. Blackard | Shortz |
| Wed, Mar 10, 1999 | 29D | It's made at fights | Wesley R. Johnson | Shortz |
| Wed, Aug 20, 1997 | 51D | Vegas transaction | Chuck Deodene | Shortz |
| Sun, Feb 18, 1996 | 31D | Reno transaction | Norma Steinberg | Shortz |
| Sat, Aug 27, 1994 | 8D | Hazard | Joy L. Wouk | Shortz |