Terence Crawford
After not fighting for over a year following the Ortiz loss, Jennings signed with Top Rank. Jennings returned to the ring on August 19, 2017, against journeyman Daniel Martz on the undercard of Terence Crawford vs. Julius Indongo. He knocked out Martz in the second round. He next fought on December 9, 2017, at the Madison Square Garden, on the undercard of Vasyl Lomachenko vs. Guillermo Rigondeaux. Where he knocked out Don Haynesworth in three rounds. His first fight of 2018 was against Akhror Muralimov on February 16. He knocked out Muralimov in the third round. Jennings’ next fight took place on April 28, 2018, where he beat Joey Dawejko by unanimous decision over ten rounds.