Offseason
- October 12, 1965: John Orsino was traded by the Orioles to the Washington Senators for Woodie Held.
- November 29, 1965: Ron Stone was drafted from the Orioles by the Kansas City Athletics in the 1965 rule 5 draft.
- December 2, 1965: Norm Siebern was traded by the Orioles to the California Angels for Dick Simpson.
- December 6, 1965: Darold Knowles and Jackie Brandt were traded by the Orioles to the Philadelphia Phillies for Jack Baldschun.
- December 9, 1965: Milt Pappas, Jack Baldschun, and Dick Simpson were traded by the Orioles to the Cincinnati Reds for Frank Robinson.
- March 10, 1966: Lou Piniella was traded by the Orioles to the Cleveland Indians for Cam Carreon.
Read more about this topic: 1966 Baltimore Orioles Season