| Date | Grid | Clue | Author |
| Sun Apr 21, 2024 | 10D | Tennis great known as "The Punisher" | Michael Schlossberg |
| Sat Jan 27, 2024 | 3D | Writer of the 2009 autobiography "Open" | Grace Warrington and Greg Warrington |
| Fri Dec 30, 2022 | 4D | Tennis great nicknamed "The Punisher" | Brendan Emmett Quigley |
| Thu Oct 20, 2022 | 9D | U.S. Open winner of 1994 and 1999 | Rebecca Goldstein |
| Mon May 3, 2021 | 13D | Tennis great Andre (3) | Ross Trudeau |
| Sun Nov 15, 2020 | 86D | Andre who won the 1994 and 1999 U.S. Opens | Caitlin Reid |
| Wed Jul 15, 2020 | 20A | Tennis player with a Career Golden Slam (winning all four majors and an Olympic gold) | Lee Higbie and Jeff Chen |
| Mon Apr 15, 2019 | 5D | Court great Andre | Patrick Blindauer and Samuel A. Donaldson |
| Wed Nov 14, 2018 | 4D | Longtime Sampras rival | Sam Trabucco |
| Fri Sep 28, 2018 | 50A | Autobiographer who wrote that tennis is "the loneliest sport" | Kameron Austin Collins |
| Sun Sep 16, 2018 | 31A | Tennis great who wrote the 2009 tell-all "Open" | Joel Fagliano |
| Sun May 20, 2018 | 65D | Four-time Australian Open winner | Will Nediger |
| Wed Nov 1, 2017 | 7A | Winner of the four tennis majors and Olympic 8-Down | Herre Schouwerwou |
| Thu Mar 10, 2016 | 49D | Andre who wrote "Open: An Autobiography" | Ed Sessa |
| Sun Feb 14, 2016 | 72A | 1990s-2000s tennis champ nicknamed "The Punisher" | Mary Lou Guizzo |
| Thu Jul 23, 2015 | 1D | Sports champion whose father twice represented Iran as an Olympic boxer | Timothy Polin |
| Wed Feb 4, 2015 | 25A | Tennis champion with the 2009 memoir "Open" | Julian Lim |
| Sun Nov 9, 2014 | 22A | 1996 Olympic tennis gold medalist | Tom McCoy |
| Mon Aug 5, 2013 | 20A | Tennis great Andre (3) | Alan Arbesfeld |
| Tue Jul 16, 2013 | 43D | Tennis's Andre | Joel Fagliano |
| Thu Apr 5, 2012 | 14A | 1992 Wimbledon winner (3) | Elizabeth C. Gorski |
| Wed Feb 29, 2012 | 14A | Sports star who wrote 2009's "Open: An Autobiography" | Kevan Choset |
| Sun Nov 20, 2011 | 86A | 2011 International Tennis Hall of Fame inductee | Trip Payne |
| Thu Sep 16, 2010 | 12D | Sports legend with the autobiography "Open" | Joey Weissbrot, Brown University '11 |
| Sat Dec 6, 2008 | 23D | Career Golden Slam winner | Ashish Vengsarkar & Narayan Venkatasubramanyan |
| Thu Jun 19, 2008 | 8D | Golf great Andre | Joe Krozel |
| Sat Jan 12, 2008 | 41D | 1994 U.S. Open winner (2) | Frederick J. Healy |
| Thu Nov 22, 2007 | 15D | Sampras rival (2) | Oliver Hill |
| Sat Aug 12, 2006 | 30A | Winner of all four majors | Patrick Berry |
| Wed May 10, 2006 | 44D | Sampras rival (2) | Kevan Choset |
| Sun Mar 26, 2006 | 8D | Tennis star with a shaved head | Patrick Berry |
| Sun Jul 4, 2004 | 154A | 1992 Wimbledon champ (2) | Elizabeth C. Gorski |
| Sat Jan 17, 2004 | 57A | Two-time U.S. Open champ (3) | Patrick Berry |
| Wed Dec 31, 2003 | 18D | Two-time U.S. Open winner | Alan Arbesfeld |
| Fri Jul 5, 2002 | 45A | Two-time U.S. Open champ (3) | Manny Nosowsky |
| Thu Jan 24, 2002 | 45D | 1999 U.S. Open champ (3) | Brendan Emmett Quigley |
| Fri Oct 19, 2001 | 58A | 1992 Wimbledon winner (3) | Joe DiPietro |
| Wed Oct 17, 2001 | 8A | 1999 U.S. Open champ (3) | Greg Staples |
| Sun Aug 12, 2001 | 22A | Winner of all four grand slam titles | Nancy Nicholson Joline |
| Sun May 13, 2001 | 88D | Two-time U.S. Open champ (3) | Nancy Nicholson Joline |
| Fri Nov 5, 1999 | 56A | 1999 U.S. Open champ (3) | Mark Diehl |
| Sat Jan 23, 1999 | 38D | 1994 U.S. Open winner (2) | Frank Longo |
| Tue Oct 28, 1997 | 10D | Tennis great Andre (3) | Bernice Gordon |
| Thu Jun 29, 1995 | 51D | Chang rival | Matt Gaffney |
| Sun Jun 25, 1995 | 112A | 1992 Wimbledon winner (3) | Frances Hansen |
| Sun May 15, 1994 | 68D | 1992 Wimbledon champ (2) | Charles M. Deber |