| Date | Grid | Clue | Author | Editor |
| Sun, Apr 21, 2019 | 21A | 1958 #1 hit in a foreign language | Grant Thackray | Shortz |
| Thu, Feb 25, 2016 | 40D | 1958 hit with the lyric "Your love has given me wings" | Joel Fagliano | Shortz |
| Thu, Dec 15, 2011 | 24D | 1958 hit that won the first-ever Grammy for Song of the Year | Jim Hilger | Shortz |
| Sun, Jul 11, 2010 | 53D | 1958 #1 hit by Domenico Modugno | Ed Sessa | Shortz |
| Thu, Aug 20, 2009 | 44D | 1958 #1 song with the lyric "Let's fly way up to the clouds" | Elizabeth C. Gorski | Shortz |
| Sun, Jan 18, 2004 | 28A | 1958 #1 song | Arlan and Linda Bushman | Shortz |
| Sun, Jun 27, 1999 | 115A | Old Plymouth | Robert Malinow | Shortz |
| Sat, Dec 26, 1998 | 16A | Travel by aeroplano | A. J. Santora | Shortz |
| Fri, Jul 17, 1998 | 44A | #1 foreign-language song of 1958 | Randolph Ross | Shortz |
| Sun, Jul 13, 1997 | 21A | Grammy-winning single of 1958 | Fred Piscop | Shortz |
| Sun, Sep 29, 1996 | 60A | To fly on Alitalia | M. Reagle | Shortz |