Gillaspie attended Millard North High School in Omaha, Nebraska, where he played baseball, football, and basketball. Gillaspie attended Wichita State University, majoring in geology, from 2006–08. He hit .362 with 58 doubles and 24 home runs over three seasons and was a three-time All-Missouri Valley Conference selection.

Gillaspie played in the Cape Cod Baseball League during the summer of 2007, leading the entire league in hitting with a .345 batting average. He led the Falmouth Commodores to the championship series against the Yarmouth-Dennis Red Sox, but could not play in the series as he had to return to school. He was named the MVP of the Cape League.

Gillaspie was drafted by the San Francisco Giants 37th overall in the 2008 Major League Baseball Draft. He played only 24 games in the minors before being called up to the majors on September 6, 2008. He got his first major league hit off Dan Haren on September 16, 2008.

Gillaspie spent 2009 at Single-A San Jose and 2010 in Double-A Richmond. He started the 2011 season with Triple-A Fresno. On June 5, 2011, Gillaspie was recalled to the major leagues when Brandon Belt was placed on the 15-day disabled list. On September 27, 2011, Gillaspie hit an inside-the-park home run against Colorado Rockies pitcher Esmil Rogers for his first Major League home run.

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