Caldeira played youth soccer with Mississauga Falcons and Erin Mills SC,[1] later joining Sigma FC.
[2] In 2022, he committed to attend West Virginia University to play for the men's soccer team.
[6][7] In September 2023, he was named the Sun Belt Conference Offensive Player of the Week.
[8] On October 18, 2023, he scored a hat trick in a 5-2 victory over the Marshall Thundering Herd.
[20] On July 30, 2021, he signed a developmental contract with Forge FC of the Canadian Premier League.