Memphis 901 On January 9, 2020, Jennings was selected with the 17th overall pick by
FC Dallas in the
2020 MLS SuperDraft. However, in late February, he was released from the club's pre-season camp without earning a first-team contract. A few months later, on July 13, Jennings joined
USL Championship club
Memphis 901. Jennings made his professional debut for Memphis 901 on July 15, coming on as a 62nd-minute substitute during a 3–0 defeat against
Birmingham Legion. He then scored his first goal for the club on July 18 against
Atlanta United 2 during a 2–2 draw. Jennings ended his first season scoring a hat-trick on October 3 against Birmingham Legion. His three goals helped the club to a 3–1 victory. This was part of a scoring run in which Jennings scored in four games in a row, netting eight goals.
Los Angeles FC On December 4, 2020, Jennings joined
USL Championship club
Indy Eleven for the
2021 season. However, on March 9, 2021, it was announced that Jennings had signed with
Major League Soccer club
Los Angeles FC without playing a game for Indy Eleven. To make the signing, Los Angeles FC traded their natural third-round selection in the
2022 MLS SuperDraft for Jennings's college rights from
FC Dallas.
Tampa Bay Rowdies On January 26, 2023, Jennings signed with USL Championship side
Tampa Bay Rowdies. He left Tampa Bay following their 2024 season.
Charleston Battery On February 18, 2025, Jennings signed with USL Championship side
Charleston Battery. On 1 December, 2025, Jennings left
Charleston Battery.
FC Ryukyu In January 2026, Jennings signed with
J3 League side
FC Ryukyu in Okinawa, Japan. ==Career statistics==