Offseason
- November 10, 1998: Scott Brosius resigned as a Free Agent with the New York Yankees.
- November 11, 1998: David Cone resigned as a Free Agent with the New York Yankees.
- November 25, 1998: Bernie Williams resigned as a Free Agent with the New York Yankees.
- February 5, 1999: Jeff Juden was signed as a Free Agent with the New York Yankees.
- February 18, 1999: Roger Clemens was traded by the Toronto Blue Jays to the New York Yankees for Homer Bush, Graeme Lloyd, and David Wells.
- March 30, 1999: Izzy Molina was traded by the Arizona Diamondbacks with Ben Ford to the New York Yankees for Darren Holmes and cash.
Read more about this topic: 1999 New York Yankees Season