| 2026-01-02 | May day celebrant |
| 2025-08-26 | Certain parent |
| 2025-03-14 | Band-Aid applier, perhaps |
| 2024-12-22 | Cry during an argument between siblings |
| 2024-08-16 | Million ___ March (political event of 2000) |
| 2024-03-28 | Palindromic family member |
| 2024-03-21 | Cry from an upset sibling |
| 2023-10-25 | Stereotypical word in a heart tattoo |
| 2023-10-20 | Cry during an argument between siblings |
| 2023-08-17 | Wow, that's upside down! |
| 2022-10-17 | Honoree of many classic tattoos |
| 2022-06-03 | Small-business partner, perhaps |
| 2022-01-06 | ___ jeans |
| 2021-08-02 | May honoree |
| 2021-07-30 | ___ jeans |
| 2021-02-11 | May day celebrant |
| 2020-12-09 | Old-fashioned tattoo |
| 2020-10-21 | Classic tattoo word |
| 2020-09-01 | Tattoo subject who might disapprove of tattoos |
| 2020-08-02 | One who delivers |
| 2020-05-31 | Stage ___ |
| 2020-05-29 | Care package sender, often |
| 2018-12-29 | Cry over spilled milk, perhaps |
| 2018-05-21 | Dad's partner |
| 2018-04-29 | Dr. ___ |
| 2018-02-15 | Hockey ___ |
| 2017-03-31 | Pop enthusiast? |
| 2017-03-14 | Pop fan? |
| 2016-11-30 | Having a baby makes one |
| 2016-06-15 | ___ jeans |
| 2015-06-29 | Word in a heart tattoo |
| 2015-04-16 | Dr. ___ |
| 2015-01-12 | ___ and pop |
| 2014-12-06 | What everyone has at birth |
| 2014-07-09 | Alice, to Dennis the Menace |
| 2013-10-06 | Pop lover |
| 2013-03-25 | May honoree |
| 2012-12-11 | May honoree |
| 2012-10-11 | May V.I.P. |
| 2012-05-22 | May honoree |
| 2011-02-10 | "Mr. ___" (1983 film) |
| 2011-01-04 | Partner of baseball and apple pie |
| 2010-07-28 | Soccer or hockey follower |
| 2010-07-06 | Blondie, to Alexander and Cookie |
| 2010-06-14 | Pop's partner |
| 2010-05-19 | May honoree |
| 2009-06-25 | Apple pie companion? |
| 2008-09-14 | MADD member |
| 2008-08-04 | T.L.C. giver |
| 2008-05-29 | MTV's "Date My ___" |
| 2008-03-04 | Stereotypical tattoo |
| 2007-12-18 | Soccer ___ |
| 2007-12-16 | One making a delivery |
| 2007-10-20 | "Mr. ___," 1983 comedy |
| 2007-08-26 | Pop's partner |
| 2007-05-28 | Soccer ___ |
| 2007-05-10 | Quaint tattoo |
| 2006-05-31 | "Go to your room!" sayer |
| 2006-04-30 | Subject of a May tribute |
| 2005-12-21 | Dispenser of 47-Across |
| 2005-11-21 | One in a union with 41-Across |
| 2005-07-24 | Noted apple pie baker |
| 2005-07-08 | Small business co-owner? |
| 2005-06-26 | Den ___ |
| 2005-05-05 | Stay-at-home ___ |
| 2004-11-10 | Soccer ___ |
| 2004-09-05 | Common cartoon tattoo |
| 2004-08-24 | S.U.V. "chauffeur," maybe |
| 2004-05-13 | May honoree |
| 2003-12-30 | May honoree |
| 2003-10-27 | Second Sunday in May honoree |
| 2003-01-25 | Delivery person? |
| 2002-08-12 | Pop's partner |
| 2002-05-31 | Soccer ___ |
| 2002-02-20 | Popular tattoo |
| 2001-12-25 | May honoree |
| 2001-11-13 | Celebrated apple-pie maker |
| 2001-06-20 | Classic tattoo |
| 2001-03-21 | Tattoo favorite |
| 2000-06-30 | Addressee of many a request |
| 1999-09-05 | Soccer ___ |
| 1999-06-16 | She has a day in May |
| 1999-06-02 | Recipient of many a televised "Hi" |
| 1998-03-17 | Tattoo word, often |
| 1997-10-08 | Small business co-owner |
| 1997-03-18 | Dad's mate |
| 1997-02-17 | "Hi ___!" (fan's message) |
| 1996-09-22 | Pop idol? |
| 1995-11-03 | May honoree |
| 1994-03-05 | It goes with apple pie |
| 1994-01-02 | Tattoo dedicatee |