| Date | Grid | Clue | Author |
| Tue Feb 13, 2024 | 63A | Apple product from 2001 to 2022 | Peter Gordon |
| Wed Feb 7, 2024 | 57D | Tech product officially discontinued in 2022 | Daniel Mauer |
| Mon Jan 22, 2024 | 63A | Apple music player discontinued in 2022 | Jake Halperin |
| Sun Sep 24, 2023 | 61A | Product once marketed with dancing silhouettes | Joel Fagliano and Christina Iverson |
| Sat Mar 18, 2023 | 27D | Nano technology, once? | Ada Nicolle |
| Fri Nov 25, 2022 | 32A | Touch, for one (2) | Simon Marotte |
| Mon Jul 18, 2022 | 55D | Once-popular Apple music player | Phoebe Gordon |
| Tue May 10, 2022 | 1A | Media player debut of 2001 | Lou Weiss |
| Wed Feb 23, 2022 | 41D | Apple product (3) | Rose Conlon |
| Wed Jan 12, 2022 | 62A | Nano or Touch | Adam Aaronson |
| Mon May 31, 2021 | 7D | Cher holder? | Michael Lieberman |
| Wed Apr 28, 2021 | 66A | Player that debuted in 2001 | Hal Moore |
| Wed Apr 21, 2021 | 51A | Popular holiday gift of 2001 | Brandon Koppy |
| Fri Apr 16, 2021 | 47A | Device outmoded by the smartphone | Tom Pepper |
| Tue Mar 23, 2021 | 55D | It can carry a tune (2) | Dan Schoenholz |
| Tue Mar 16, 2021 | 44D | ___ Touch (2) | Lindsey Hobbs |
| Sun Oct 25, 2020 | 114D | Gadget that once came with a click wheel | Peter A. Collins |
| Fri Mar 27, 2020 | 3D | Album holder | Kyle Dolan |
| Sun Feb 24, 2019 | 78D | Mini, for one (2) | Erik Agard |
| Thu Feb 14, 2019 | 2D | Product whose introduction was music to people's ears? | John E. Bennett and Jeff Chen |
| Mon Nov 19, 2018 | 62A | Apple device with earbuds | Jim Hilger |
| Sun Sep 23, 2018 | 106D | Device outmoded by smartphones | Andrew Zhou |
| Wed Jul 4, 2018 | 56A | Device sold with earbuds | Freddie Cheng |
| Sun Jul 16, 2017 | 89D | Apple debut of 2001 | Andrea Carla Michaels and Pete Muller |
| Tue May 17, 2016 | 5A | Listening device? | Paula Gamache |
| Fri Jan 22, 2016 | 5D | Light music source? | Paula Gamache |
| Tue Oct 6, 2015 | 1D | Device with earbuds | Zhouqin Burnikel |
| Wed Aug 12, 2015 | 28D | Apple's ___ Touch | Tom McCoy |
| Tue Aug 4, 2015 | 39D | Device that can be linked to an auto stereo | Joel Fagliano |
| Sun Jul 12, 2015 | 46D | Device once sold in a U2 Special Edition | Patrick Berry |
| Sun May 3, 2015 | 107A | Shuffle, e.g. | Dan Schoenholz |
| Wed Apr 22, 2015 | 27A | With 32-Down, Apple release of 2005 | Alex Vratsanos and Sam Ezersky |
| Tue Oct 7, 2014 | 29D | Apple music player | Matt Skoczen and Victor Fleming |
| Tue Sep 9, 2014 | 57D | "Mini" music player | Ed Sessa |
| Fri Dec 6, 2013 | 7D | Many a museum audio guide | Elizabeth C. Gorski |
| Tue Nov 19, 2013 | 22D | Music lover's carry-along | David J. Kahn |
| Sun Oct 6, 2013 | 52D | Player in a pocket | Patrick Berry |
| Thu Jul 18, 2013 | 63A | Item clipped on a waistband, perhaps | Todd Gross and David Steinberg |
| Thu Apr 25, 2013 | 8D | ___ Touch (2) | Jeffrey Wechsler |
| Thu Jan 10, 2013 | 25D | Mini, for one (2) | Kevan Choset |
| Sun Dec 9, 2012 | 12D | Device with a click wheel | Patrick Berry |
| Tue Aug 28, 2012 | 48D | ___ Shuffle | Lou Borenstein |
| Tue Dec 20, 2011 | 55D | Destination for many a music download | Julian Lim |
| Sun Dec 4, 2011 | 6A | Modern record holder? | Kelsey Blakley |
| Mon Nov 14, 2011 | 59A | Portable product for music lovers | Mark Feldman |
| Fri Oct 7, 2011 | 1A | Brainchild of 57-Across | Kevin G. Der |
| Sat May 21, 2011 | 20D | Touch, e.g. (3) | Barry C. Silk |
| Thu May 12, 2011 | 38D | Gadget whose name was inspired by "2001: A Space Odyssey" | Patrick John Duggan |
| Sun Jan 23, 2011 | 34A | *Touch, e.g. (3) | Chris A. McGlothlin |
| Sun Mar 14, 2010 | 7D | Touch, for one (2) | Caleb Madison |
| Sun Jan 17, 2010 | 37D | Touch, e.g. (3) | Cathy Allis |
| Sun Dec 13, 2009 | 107D | It can carry a tune (2) | Mike Shenk |
| Mon Nov 2, 2009 | 55D | Apple MP3 player | Andrea Carla Michaels and Kent Clayton |
| Mon Aug 24, 2009 | 7D | Item with earbuds | Anthony J. Salvia |
| Tue Mar 24, 2009 | 33D | Popular MP3 player (2) | Pancho Harrison |
| Sun Feb 22, 2009 | 71D | Song holder (2) | Barry C. Silk & Doug Peterson |
| Tue Feb 3, 2009 | 55D | Music device with earbuds | Katie Yeager |
| Sat Jan 17, 2009 | 55A | Player in a docking station | Brad Wilber |
| Sat Oct 4, 2008 | 10A | Mini, e.g. | Matt Ginsberg |
| Sun Jul 27, 2008 | 12A | It's found in many pockets nowadays | Mike Nothnagel and David Quarfoot |
| Thu Jul 10, 2008 | 16A | Shuffle or 67-Across, e.g. | Ari Halpern |
| Fri Feb 22, 2008 | 54A | Holder of many tracks | Mike Nothnagel and David Quarfoot |
| Thu Dec 6, 2007 | 12D | Product with earbuds (2) | Joe Krozel |
| Mon Nov 5, 2007 | 30D | Its first ad touted "1,000 songs in your pocket" | Jeremy Horwitz |
| Wed Jan 10, 2007 | 17A | Product with earbuds (2) | Curtis Yee |
| Fri Dec 22, 2006 | 29D | It can help you carry a tune | Mike Nothnagel |
| Wed Dec 6, 2006 | 1D | Popular MP3 player (2) | Levi Denham |
| Tue Oct 10, 2006 | 32D | Device with a Nano model | Tyler Hinman |
| Thu Jul 13, 2006 | 53D | Song holder (2) | Manny Nosowsky |
| Sun May 7, 2006 | 88D | Device with a scroll wheel | Trip Payne |
| Mon Apr 17, 2006 | 16A | Music box? | Larry Paul |
| Sun Nov 20, 2005 | 11A | Popular player since 2001 | Patrick Merrell |
| Sat Aug 27, 2005 | 51A | Apple product (3) | Byron Walden |
| Fri Oct 1, 2004 | 11D | Apple product (3) | Bob Peoples |
| Sun Apr 25, 2004 | 19A | Apple product for audiophiles | Elizabeth C. Gorski |