Jacksonville State During his first collegiate season in 2021, Caldwell played in three games, completing 14 of his 30 pass attempts for 136 yards, while also rushing for 27 yards and a touchdown. After the conclusion of the 2021 season, he decided to enter his name into the NCAA transfer portal.
Gardner–Webb Caldwell transferred to play for the
Gardner–Webb Runnin' Bulldogs. During his two seasons at Gardner–Webb from 2022 through 2023, he completed 114 of his 183 passes for 1,083 yards and six touchdowns. After the conclusion of the 2023 season, Caldwell decided to once again enter his name into the NCAA transfer portal.
Troy Caldwell transferred to play for the
Troy Trojans. In week twelve of the 2024 season, he completed 26 of 32 passes for 288 yards, while totaling four touchdowns, in a victory versus
Georgia Southern. Caldwell finished the 2024 season, appearing in ten games, completing 63.2 percent of his passes for 1,608 yards, 13 touchdowns and eight interceptions, while also adding five scores on the ground. After the conclusion of the 2024 season, he decided to enter his name into the NCAA transfer portal for the third time.
Texas Caldwell transferred to play for the
Texas Longhorns. In Week 9 of the 2025 season, he threw a 10-yard game-winning touchdown to
Emmett Mosley in the overtime win over
Mississippi State.
Statistics ==Professional career==