In his first start with the Orioles, Jimenez threw six innings against the Red Sox, getting tagged for four runs and a loss. He would go on to lose his next three decisions, as the Orioles lost in his first five starts. He pitched to a 6.59 ERA and went 0–4 in his first month with the O's. His first win as a member of the Orioles came on May 2, when he tossed 7 scoreless innings against the Twins. On July 11, 2014, Jimenez was placed on the 15-day DL due to a right ankle sprain.