Offseason
- October 15, 1968: Steve Barber was drafted from the Yankees by the Seattle Pilots as the 37th pick in the 1968 MLB expansion draft.
- October 21, 1968: Jim Bouton was purchased from the Yankees by the Seattle Pilots.
- December 2, 1968: Billy Cowan was drafted by the Yankees from the Philadelphia Phillies in the 1968 rule 5 draft.
- December 4, 1968: Andy Kosco was traded by the Yankees to the Los Angeles Dodgers for Mike Kekich.
- December 6, 1968: Charley Smith was traded by the Yankees to the San Francisco Giants for Nate Oliver.
- January 8, 1969: John Orsino was purchased by the Yankees from the Washington Senators.
- Prior to 1969 season: Merritt Ranew was acquired from the Yankees by the Seattle Pilots.
Read more about this topic: 1969 New York Yankees Season