He played in Major League Baseball (MLB) for the Cleveland Indians, Arizona Diamondbacks, Houston Astros, and Washington Nationals.

Sipp made his professional debut in 2004 with the Low-A Mahoning Valley Scrappers, logging a 3–1 record and 3.16 ERA in 10 appearances.

He split the 2005 season between the Single-A Lake County Captains and the High-A Kinston Indians, posting a 6–3 record and 2.40 ERA in 35 games between the two teams.

On December 12, 2012, Sipp was acquired by the Arizona Diamondbacks in a nine-player three-team blockbuster trade that sent Shin-Soo Choo to the Cincinnati Reds.

On February 7, 2014, Sipp signed a minor league deal with the San Diego Padres organization.

[10] He was assigned to the Triple-A El Paso Chihuahuas to begin the season but was released on May 1 after pitching to a 4.30 ERA in 11 appearances.

[11] Sipp became a key component of the Astros' bullpen for the remainder of the 2014 season, posting a 2.94 xFIP and striking out 11.19 batters per nine innings of work.

Reports involving the Houston Astros sign stealing scandal state that prior to the 2019 World Series Nationals ace Max Scherzer reached out to Sipp and asked if the Nationals needed to be concerned about the Astros even with no runners on base, to which Sipp replied yes.