A native of Aurora, Illinois, Kipper, a left-hander, stood 6 feet 2 inches (1.88 m) tall and weighed 200 pounds (91 kg) during his active career. After graduating from Aurora Central Catholic High School, he was selected by the California Angels with the eighth pick in the first round of the 1982 Major League Baseball Draft. He had signed to play baseball at Nebraska before his selection. Kipper led the Class A California League in wins (18) and earned run average (2.04) as his league\'s "pitcher of the year" in 1984. He made his MLB debut with the Angels in April 1985 at age 20, but was ineffective in two games pitched and was returned to the minor leagues. Then, on August 16, 1985, the contending Angels included Kipper in a six-player trade with the Pittsburgh Pirates that netted them veterans John Candelaria, George Hendrick and Al Holland. Kipper would pitch in 247 games for the Pirates over all or parts of seven seasons (1985–91)—initially as a starter, but then as a relief specialist—before finishing his MLB career for the Minnesota Twins in 1992.\n', '

In his eight-season MLB career, Kipper posted a 27–37 record with a 4.43 ERA and 11 saves in 271 appearances. He allowed 527 hits and 217 bases on balls, with 369 strikeouts, and 562 innings pitched.\n', '

Following his playing retirement, Kipper has worked as a pitching coach in independent league baseball and in the minor leagues. A member of the Boston Red Sox organization since 1999, he has coached for their Lowell Spinners (1999), Augusta GreenJackets (2000–01), Greenville Drive (2005–06; 2008–09; 2018), Lancaster JetHawks (2007), Portland Sea Dogs (2003–04; 2010–14), and Pawtucket Red Sox (2015–17) affiliates, working with teams from short-season leagues to Triple-A.\n', '

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