Timmons attended Brandon High School in Brandon, Florida, and the University of Tampa, where he played college baseball for the Tampa Spartans. In 1990, he played collegiate summer baseball with the Falmouth Commodores of the Cape Cod Baseball League. He was selected by the Chicago Cubs in the fifth round of the 1991 MLB draft.
Timmons made his MLB debut with the Cubs on April 26, 1995. The Cubs traded Timmons and Jay Peterson to the Cincinnati Reds for Curt Lyons on March 31, 1997. He signed with the Seattle Mariners for the 1999 season, the Tampa Bay Devil Rays for the 2000 season, and was purchased by the Chunichi Dragons of Nippon Professional Baseball's Central League for the 2001 season.
He served as the hitting coach for the Tampa Bay Rays‘ Triple-A affiliate Durham Bulls, prior to being promoted to the parent-club Rays, as their first base coach, for the 2018 season.

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