| Date | Grid | Clue | Author |
| Fri Apr 12, 2024 | 58A | Paul who wrote "Puppy Love" | Evan Kalish |
| Mon Jan 22, 2024 | 43A | Singer Paul with the memoir "My Way" | Jake Halperin |
| Fri Dec 1, 2023 | 4D | Paul who sang with Sam Cooke and Neil Sedaka on the 1963 album "3 Great Guys" | Jem Burch |
| Thu Oct 5, 2023 | 5D | Canadian-born crooner Paul | Daniel Bodily |
| Mon Jul 3, 2023 | 64A | "Puppy Love" singer Paul (3) | Sam Buchbinder |
| Fri Jun 23, 2023 | 16A | Singer/songwriter Paul | Kunal Nabar |
| Fri Jun 9, 2023 | 23A | Singer with the 1960 #2 hit "Puppy Love" | Robyn Weintraub |
| Sun Dec 25, 2022 | 71D | "My Way" lyricist Paul (3) | John Martz |
| Mon Jun 20, 2022 | 5A | Singer Paul with a star on Canada's Walk of Fame | Christopher Youngs |
| Fri Oct 29, 2021 | 57D | "Puppy Love" singer, 1960 (4) | Aimee Lucido |
| Mon Sep 27, 2021 | 5A | Paul who sang "Diana" and "Lonely Boy" | Zachary David Levy |
| Sun Feb 7, 2021 | 60D | He wrote lyrics to "My Way" for Sinatra | Katie Hale and Christina Iverson |
| Sun Jan 31, 2021 | 68A | "Lonely Boy" singer, 1959 | Jim Hilger |
| Mon Dec 21, 2020 | 63D | Singer/lyricist Paul | Sarah Keller and Derek Bowman |
| Sat Jun 6, 2020 | 49D | Pop star with top 40 hits in the 1950s, '60s, '70s and '80s | Doug Peterson |
| Sat Dec 28, 2019 | 55A | "Put Your Head on My Shoulder" singer, 1959 (2) | Robyn Weintraub |
| Mon Aug 20, 2018 | 7D | "My Way" lyricist Paul (3) | Peter Gordon |
| Sun Apr 15, 2018 | 78D | "Eso Beso" singer | Alex Bajcz |
| Sat Apr 14, 2018 | 43A | Collaborator with Sedaka and Cooke on the 1964 album "3 Great Guys" | Sam Ezersky |
| Tue Apr 10, 2018 | 70A | "Puppy Love" hitmaker, 1960 | Alan Arbesfeld |
| Sun Dec 17, 2017 | 38D | Paul who sang "Lonely Boy" (2) | Andrew J. Ries |
| Sat Dec 16, 2017 | 18A | Singer/songwriter on Canada's Walk of Fame | Sam Ezersky |
| Mon Oct 2, 2017 | 71A | Paul who sang "Eso Beso" (2) | Trenton Charlson |
| Sun Feb 19, 2017 | 37A | "Puppy Love" singer, 1960 (4) | Bruce Haight |
| Wed Jan 4, 2017 | 60A | "Diana" singer Paul (2) | Samuel A. Donaldson |
| Wed Aug 3, 2016 | 61D | "My Way" lyricist Paul (3) | Neville Fogarty |
| Sat Jun 11, 2016 | 52D | "Annette Sings ___" (1960 pop album) | Andrew Kingsley |
| Tue Jan 26, 2016 | 45A | Paul who sang "Eso Beso" (2) | Sam Ezersky |
| Mon Mar 9, 2015 | 4D | Paul with the #1 hit "Lonely Boy" | Debbie Ellerin |
| Tue Dec 16, 2014 | 59A | Paul who sang "Diana" (3) | Joel D. Lafargue |
| Thu Dec 4, 2014 | 29A | Singer on Canada's Walk of Fame since 2005 | Kacey Walker and David Quarfoot |
| Sun Nov 30, 2014 | 119A | Paul who composed the "Tonight Show" theme | Matt Ginsberg |
| Wed Aug 20, 2014 | 57D | "My Way" lyricist (6) | Zhouqin Burnikel |
| Thu May 15, 2014 | 25D | "Puppy Love" crooner | John Lieb |
| Thu Feb 20, 2014 | 51D | Paul in the Songwriters Hall of Fame | Zhouqin Burnikel and Don Gagliardo |
| Wed Jul 10, 2013 | 62A | Paul who sang "Put Your Head on My Shoulder" (2) | Ed Sessa |
| Tue Jul 2, 2013 | 26D | Paul who sang "Lonely Boy" (2) | Daniel Raymon |
| Thu May 30, 2013 | 65A | "You Are My Destiny" singer (4) | Julian Lim |
| Wed May 22, 2013 | 64A | "My Way" lyricist (6) | Kevin Christian |
| Wed Feb 20, 2013 | 8D | 1950s heartthrob Paul | John Farmer |
| Sat Oct 1, 2011 | 10D | Canadian singer with three #1 Billboard hits | David Quarfoot |
| Sat Sep 3, 2011 | 5D | "Tonight My Love, Tonight" singer | Peter Wentz |
| Wed Aug 18, 2010 | 37A | "You Are My Destiny" singer, 1958 (2) | Alex Boisvert |
| Fri Feb 12, 2010 | 24D | He had a #4 hit with "It's Time to Cry" | Kevin G. Der |
| Mon Jan 25, 2010 | 56D | Paul who wrote "My Way" (2) | Holden Baker |
| Mon Dec 28, 2009 | 57D | Paul who wrote "My Way" (2) | Patrick Merrell |
| Mon Oct 5, 2009 | 32D | Paul who sang "Diana" (3) | Mark Feldman |
| Sun Aug 30, 2009 | 3D | "It's Time to Cry" singer, 1959 | Ashish Vengsarkar and Narayan Venkatasubramanyan |
| Thu Jan 22, 2009 | 31D | "My Way" songwriter (5) | Gary J. Whitehead |
| Sun May 11, 2008 | 62A | "Puppy Love" singer, 1960 (4) | Tony Orbach and Patrick Blindauer |
| Sun Jan 6, 2008 | 94A | "My Way" lyricist (6) | Lynn Lempel |
| Mon Dec 17, 2007 | 50D | Paul who sang "Put Your Head on My Shoulder" (2) | Richard Chisholm |
| Mon Nov 12, 2007 | 15A | Paul who sang "Puppy Love" | Harvey Estes |
| Sun Aug 5, 2007 | 17D | "Lonely Boy" singer/writer | Caroline Leong |
| Tue Mar 20, 2007 | 50A | "Diana" singer (3) | Laura A. Halper |
| Mon Dec 4, 2006 | 63A | "Puppy Love" singer Paul (3) | Richard Chisholm |
| Fri Nov 17, 2006 | 42A | Classic singer with the 2005 album "Rock Swings" | Beth Hinshaw |
| Sun Sep 17, 2006 | 71D | "Lonely Boy" singer (4) | Brendan Emmett Quigley |
| Tue Sep 6, 2005 | 25D | 44-Down singer | Barry C. Silk |
| Thu Sep 1, 2005 | 15A | "Put Your Head on My Shoulder" singer, 1959 (2) | Kevan Choset |
| Wed Aug 17, 2005 | 64A | Singer Paul (6) | Kyle Mahowald |
| Wed Oct 27, 2004 | 54D | Singer Paul (6) | Nathaniel Weiss |
| Thu Jun 24, 2004 | 64A | "My Way" lyricist (6) | Patrick Merrell |
| Thu Jan 15, 2004 | 67A | Ottawa-born singer/songwriter | Patrick Merrell |
| Sat Dec 20, 2003 | 26A | "My Way" lyricist (6) | Myles Callum |
| Mon Nov 3, 2003 | 64A | "Puppy Love" singer Paul (3) | Marjorie Berg |
| Sun May 11, 2003 | 59D | "Dance On Little Girl" singer (2) | Patrick Berry |
| Wed May 7, 2003 | 44D | "Diana" singer (3) | Alan Arbesfeld |
| Tue Apr 29, 2003 | 17A | "Diana" crooner Paul | Norma Johnson |
| Wed Dec 18, 2002 | 52D | "My Way" writer (2) | Merle Baker |
| Mon Sep 30, 2002 | 62A | Paul who sang "Diana" (3) | Harvey Estes and Nancy Salomon |
| Mon Sep 9, 2002 | 53D | "Lonely Boy" singer Paul | William I. Johnston |
| Tue Dec 4, 2001 | 44A | "Diana" singer Paul (2) | Michael Shteyman |
| Tue Nov 13, 2001 | 4D | "Puppy Love" singer (2) | Nancy Salomon and Bob Peoples |
| Mon Sep 25, 2000 | 37D | "My Way" songwriter (5) | Peter Gordon |
| Mon Jun 26, 2000 | 35A | Singer Paul (6) | Peter Gordon |
| Fri Jun 2, 2000 | 25D | Singer Paul (6) | Manny Nosowsky |
| Thu May 11, 2000 | 59A | "Times of Your Life" singer | Peter Abide |
| Sat Oct 23, 1999 | 56D | "Lonely Boy" singer (4) | Frank Longo and Brendan Quigley |
| Thu Sep 23, 1999 | 54D | "She's a Lady" songwriter (2) | Brendan Emmett Quigley |
| Sat May 1, 1999 | 57D | "She's a Lady" songwriter (2) | Rich Norris |
| Tue Mar 30, 1999 | 24A | "You Are My Destiny" singer, 1958 (2) | Randy Sowell |
| Sun Sep 20, 1998 | 11D | "Crazy Love" singer | Charles M. Deber |
| Sun Sep 6, 1998 | 105A | "Puppy Love" singer (2) | Rich Norris |
| Tue May 26, 1998 | 1D | "Put Your Head on My Shoulder" singer (2) | Jonathan Schmalzbach |
| Wed Apr 15, 1998 | 11D | "My Way" writer (2) | Michael S. Maurer |
| Sun Jan 25, 1998 | 81A | Old "Tonight Show" theme writer | Dave Tuller |
| Wed Oct 8, 1997 | 11D | "My Way" songwriter (5) | Gilbert H. Ludwig |
| Sun Sep 14, 1997 | 115A | "My Way" songwriter (5) | Frank Longo |
| Sun Sep 7, 1997 | 89A | 50's-60's teen idol | Randolph Ross |
| Tue Aug 12, 1997 | 55A | "Dance On Little Girl" singer (2) | Janet R. Bender |
| Mon Jan 6, 1997 | 1D | Paul who sang "Having My Baby" | S. L. Robbins |
| Sat Jan 4, 1997 | 53D | Singer who appeared in "The Longest Day" | M. W. Perry |
| Tue Dec 31, 1996 | 41D | Singer Paul (6) | A. S. Verdesca |
| Wed Dec 18, 1996 | 63D | "Lonely Boy" singer (4) | M. W. Perry |
| Sun Sep 15, 1996 | 43A | "You Are My Destiny" singer (4) | A. K. Justin |
| Thu Jul 18, 1996 | 57D | "You Are My Destiny" singer (4) | W. R. Williams |
| Wed Jul 3, 1996 | 27D | Singer Paul (6) | F. Heaney |
| Tue Feb 13, 1996 | 65A | "My Way" lyricist (6) | G. Paul |
| Tue Jul 4, 1995 | 47D | "Lonely Boy" singer (4) | Fran & Lou Sabin |
| Fri Jun 30, 1995 | 16A | "You Are My Destiny" singer (4) | Rich Norris |
| Sun Jun 18, 1995 | 96A | "My Way" songwriter (5) | Rich Norris |
| Sat Apr 1, 1995 | 65A | "Johnny's Theme" cowriter | Fred Piscop |
| Sun Mar 12, 1995 | 5D | "Puppy Love" singer, 1960 (4) | Charles M. Deber |
| Sun Nov 13, 1994 | 61A | "Put Your Head on My Shoulder" singer (2) | Frank A. Longo |
| Sun Dec 12, 1993 | 113D | "Diana" singer (3) | Cathy Millhauser |
| Wed Dec 1, 1993 | 68A | He wrote "My Way" for Sinatra | Tap Osborn |