After finishing out of play-off contention in the 2013 season, Showalter led the Orioles to a first-place finish in their division in 2014. The Orioles subsequently swept the Detroit Tigers (3-0) in the ALDS for Showalter's first major league ALDS title, before being swept themselves by the Kansas City Royals in the ALCS. On November 11, 2014, Showalter won his third AL Manager of the Year award, his first since 2004.

This August 3, 2010 Baltimore Orioles vs. Los Angeles Angels of Anaheim ticket, from Showalter's Orioles debut, was signed in blue by Showalter. This item includes a Great Moments COA.