| Date | Grid | Clue | Author | Editor |
| Mon, Jan 01, 2024 | 44D | Villain on the high seas | Harry Zheng | Shortz |
| Thu, Dec 08, 2022 | 47D | One with an "eye patch," hook hand and peg leg, as represented in this puzzle's grid | Grant Thackray | Shortz |
| Wed, Nov 11, 2020 | 19A | Download without paying, say | Alex Bajcz | Shortz |
| Sun, Sep 27, 2020 | 89D | Hook, for one | Alex Eaton-Salners | Shortz |
| Fri, Oct 27, 2017 | 21A | Steal | David Steinberg | Shortz |
| Fri, Dec 11, 2015 | 2D | Sea menace | Barry C. Silk | Shortz |
| Mon, Oct 05, 2015 | 46D | Jack Sparrow or Captain Hook | Mike Buckley | Shortz |
| Wed, Sep 09, 2015 | 27A | Copy illegally | Michael Hawkins | Shortz |
| Fri, Aug 21, 2015 | 15A | Sea menace | David Steinberg | Shortz |
| Mon, Jul 27, 2015 | 47D | Jolly Roger flier | D. Scott Nichols and Zhouqin Burnikel | Shortz |
| Sun, Jan 29, 2012 | 110A | One taking the gold? | Ian Livengood | Shortz |
| Fri, May 28, 2010 | 25D | Take the wrong way? | Joe Krozel | Shortz |
| Thu, Jan 24, 2008 | 2D | Capt. Sparrow, e.g. | Matt Ginsberg | Shortz |
| Fri, Jun 01, 2007 | 1D | Marine menace | David Quarfoot and Katy Swalwell | Shortz |
| Sun, Feb 18, 2007 | 83A | Copy illegally | David Kwong and Kevan Choset | Shortz |
| Sat, Apr 29, 2006 | 4D | Take illegally | Robert H. Wolfe | Shortz |
| Sun, Nov 07, 2004 | 76A | Copy illegally | Con Pederson | Shortz |
| Mon, May 17, 2004 | 40A | One sailing under a skull and crossbones | Ethan Cooper | Shortz |
| Mon, Oct 30, 2000 | 42A | Jolly Roger flier | Gregory E. Paul | Shortz |
| Sat, Oct 02, 1999 | 32D | Plagiarist | Rich Norris | Shortz |
| Fri, Dec 18, 1998 | 44D | Gilbert and Sullivan extra | Manny Nosowsky | Shortz |
| Wed, Sep 18, 1996 | 45D | Willie Stargell, e.g. | D. J. Kahn | Shortz |
| Thu, Mar 14, 1996 | 18D | Copyright violator | R. Silvestri | Shortz |
| Sat, Jun 17, 1995 | 39D | Use without permission | Frank A. Longo | Shortz |