Born in Pascagoula, Mississippi, Sipp graduated from Moss Point High School in Moss Point, Mississippi, where he also competed in football, winning a state title with the team in 2000. In baseball, Sipp also helped Moss Point High reach the state championship in baseball. Sipp and fellow major leaguer Joey Butler formerly played against one another, as they are both from Jackson County, Mississippi. Sipp played for Mississippi Gulf Coast Community College, and also attended Okaloosa-Walton College, before transferring to Clemson University.\n', '

After being drafted by Cleveland in the 45th round in 2004, Sipp played with the Mahoning Valley Scrappers, Lake County Captains, Kinston Indians, Akron Aeros, and Columbus Clippers.\n', '

He made his major league debut on April 22, 2009. Coming out of the bullpen, Sipp went 2–0 with an ERA of 2.92, recording 48 strikeouts. In 4 years in the Indians bullpen, he appeared in 248 games and recorded 167 holds, striking out 225 batters and recording a 3.68 ERA.\n', '

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