Drafted by the Baltimore Orioles in the 9th round of the 2009 MLB Draft from Rice University. Started in the minors with the single-A Delmarva Shorebirds, posting a 3.50 ERA in eight games started and 46.1 innings pitched. Was then called up to the Frederick Keys to finish the season, putting up a 2-2 record with a 3.04 ERA and 71 innings pitched with 63 strikeouts and 25 walks. In 2011, Berry started the season with the Gulf Coast League Orioles before being sent to the single-A Aberdeen IronBirds, placing a 4.84 ERA with 33.2 innings pitched and 19 strikeouts in 10 games.

In 2012,  Berry began the year with the Frederick Keys, going 2-4 in 36 games out of the bullpen with a 3.36 ERA in 67.0 innings pitched before being called up to the double-A Bowie Baysox and pitching in one game, going three scoreless innings.