Several blockbusters in this list.
- July 29, 2018. The New York Yankees traded Giovanny Gallegos and Chasen Shreve to the St. Louis Cardinals for Luke Voit and international bonus slot money.
- June 15, 2004. The New York Yankees sent Nerio Rodriguez to the St. Louis Cardinals as part of a conditional deal.
- August 22, 2003. The New York Yankees traded Sterling Hitchcock to the St. Louis Cardinals for Ben Julianel (minors) and Justin Pope (minors).
- December 21, 1995. The St. Louis Cardinals purchased Rick Honeycutt from the New York Yankees.
- August 31, 1993. The New York Yankees traded Rich Batchelor to the St. Louis Cardinals for Lee Smith.
- July 16, 1985. The New York Yankees purchased Neil Allen from the St. Louis Cardinals.
- December 14, 1982. The St. Louis Cardinals traded Stan Javier and Bob Meacham to the New York Yankees for Steve Fincher (minors), Bob Helsom (minors) and Marty Mason (minors).
- October 21, 1981. The New York Yankees traded Willie McGee to the St. Louis Cardinals for Bob Sykes.
- February 16, 1981. The New York Yankees traded Rafael Santana to the St. Louis Cardinals for a player to be named later. The St. Louis Cardinals sent George Frazier (June 7, 1981) to the New York Yankees to complete the trade.
- April 30, 1980. The St. Louis Cardinals purchased Jim Kaat from the New York Yankees.
- June 13, 1975. The St. Louis Cardinals purchased Mike Wallace from the New York Yankees.
- September 6, 1973. The St. Louis Cardinals purchased Matty Alou from the New York Yankees.
- August 7, 1973. The New York Yankees traded a player to be named later and cash to the St. Louis Cardinals for Wayne Granger. The New York Yankees sent Ken Crosby (September 12, 1973) to the St. Louis Cardinals to complete the trade.
- March 30, 1973. The New York Yankees sent Wade Blasingame to the St. Louis Cardinals as part of a conditional deal.
- December 8, 1966. The St. Louis Cardinals traded Charley Smith to the New York Yankees for Roger Maris.
- January 13, 1965. The New York Yankees purchased Paul Toth from the St. Louis Cardinals.
- October 4, 1961. The New York Yankees traded Frank Leja to the St. Louis Cardinals for Ben Mateosky (minors).
- May 12, 1959. The St. Louis Cardinals purchased Jack Urban from the New York Yankees. (Date given is approximate. Exact date is uncertain.)
- June 14, 1958. The St. Louis Cardinals purchased Sal Maglie from the New York Yankees.
- April 11, 1954. The St. Louis Cardinals traded Enos Slaughter to the New York Yankees for Emil Tellinger (minors), Bill Virdon and Mel Wright.
- February 23, 1954. The St. Louis Cardinals purchased Vic Raschi from the New York Yankees for $85,000.
- May 14, 1951. The St. Louis Cardinals traded Don Bollweg and $15,000 to the New York Yankees for Billy Johnson.
- May 15, 1950. The St. Louis Cardinals purchased Johnny Lindell from the New York Yankees.
- March 26, 1935. The New York Yankees purchased Pat Malone from the St. Louis Cardinals for $15,000.
- July 23, 1915. The New York Yankees purchased Elmer Miller from the St. Louis Cardinals.
- August 25, 1913. The New York Yankees purchased Frank Gilhooley from the St. Louis Cardinals.
- April, 1906. The St. Louis Cardinals purchased Ambrose Puttmann from the New York Highlanders.