The first issue of Sports Illustrated was release on August 16, 1954. Over the past 55 years, the New York Yankees have had the most covers by any sports team, with a total of 66.
There were two All-Star Game issues that I didn’t include in the collage below, because it wasn’t solely Yankees related. If you care to see them: July 07, 1958 | Volume 9, Issue 1 & July 09, 1956 | Volume 5, Issue 2
I searched through the SI Vault and dug up every issue of the magazine with a Yankee related cover. I hope you like it.