[2] After graduating high school, Jennings enrolled at the University of Central Florida and joined the UCF Knights college soccer team.
[4] During his final season with the Knights, Jennings scored 18 goals in 20 matches, earning several individual accolades.
[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.
[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.
[14] On January 26, 2023, Jennings signed with USL Championship side Tampa Bay Rowdies.