Drafted by the Minnesota Twins in the 17th round of the 1987 MLB amateur draft, Hale made his Major League Baseball debut with the Twins on August 27, 1989, and appeared in his final game October 2, 1997.
Chip Hale is associated with one of the most famous bloopers in baseball history. On May 27, 1991, while playing for the Class AAAPortland Beavers, he hit a deep fly ball to right where outfielder Rodney McCray attempted to catch the ball and ran through the wall.
In 2009, Hale was hired to be the third base coach for the New York Mets. He was a candidate to become manager of the Mets after Jerry Manuel was fired at the end of the 2010 season, however, the position went to Terry Collins.
On October 5, 2011, Hale signed a two-year deal to become Bench Coach of the Oakland Athletics  He was replaced by Tim Teufel.