After being released by the Padres on May 1, 2014, the lefty reliever and veteran of five seasons joined the Astros' bullpen and enjoyed immediate success. Posting a 2.66 ERA and 0.962 WHIP in 116 games in two seasons with the Astros, Sipp inked a three-year contract worth $18 million to stay in Houston.

His production suffered in 2016 and 2017 but he had a bounceback year in 2018. Over those five seasons in Houston, Sipp posted an 11-11 record with a 3.49 ERA and five saves. Left off the 2017 postseason roster due to ineffectiveness, Sipp did appear in nine postseason games for the Astros during 2015 and 2018, registering an 0-1 mark with a 0.00 ERA in 6-2/3rd innings.

The Mississippi native has pitched 11 seasons through 2019, compiling a 26-22 record with a 3.72 ERA and seven saves.