After graduating high school, Jennings enrolled at the University of Central Florida and joined the UCF Knightscollege soccer team. He made his debut on August 26, 2016, against the Grand Canyon Antelopes.[3] He scored his first and only goal of his freshman season on October 8 against the Memphis Tigers in a 2–3 defeat.[3] During the 2017 season, Jennings scored 7 goals in 16 matches.[3] The next season, Jennings had a breakout season, scoring 20 goals and starting all 18 matches for the Knights.[4] He ended the season tied as the NCAA Division I top-scorer.[4]
During his final season with the Knights, Jennings scored 18 goals in 20 matches, earning several individual accolades.[4] He was named a semifinalist for the Hermann Trophy for the 2019 season.[4]
Club career
Memphis 901
On January 9, 2020, Jennings was selected with the 17th overall pick by FC Dallas in the 2020 MLS SuperDraft.[5] However, in late February, he was released from the club's pre-season camp without earning a first-team contract.[6] A few months later, on July 13, Jennings joined USL Championship club Memphis 901.[7]
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.[8] He then scored his first goal for the club on July 18 against Atlanta United 2 during a 2–2 draw.[9]
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.[10] This was part of a scoring run in which Jennings scored in four games in a row, netting eight goals.[11]
Los Angeles FC
On December 4, 2020, Jennings joined USL Championship club Indy Eleven for the 2021 season.[12] 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.[13] 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.[13] Following the 2022 season, Jennings was released by LAFC.[14]
Tampa Bay Rowdies
On January 26, 2023, Jennings signed with USL Championship side Tampa Bay Rowdies.[15] He left Tampa Bay following their 2024 season.[16]