Oliver was drafted by the Minnesota Twins in the 17th round of the 2006 Major League Baseball Draft, but did not sign, opting instead to attend Oklahoma State University, where he played on the Oklahoma State Cowboys baseball team.

Oliver pitched for the Durham Bulls of the Triple-A International League, until he opted out of his contract in July and was granted free agency.

He made 16 appearances for the Triple-A Norfolk Tides, logging a 3.72 ERA with 34 strikeouts in 29 innings pitched.

[14] On December 15, 2016, Oliver signed a minor league contract with the Milwaukee Brewers that included an invitation to spring training.

[15] In 16 games for the Triple-A Colorado Springs Sky Sox, he struggled to a 7.59 ERA with 20 strikeouts across 21+1⁄3 innings pitched.