Caldwell was born in Hampshire and began karting in 2013 at the age of eleven. He raced in karts for four seasons, finishing third in the 2016 Rotax Euro Challenge and participating in the Rotax Max Challenge Grand Finals, representing Great Britain.
In 2016, Caldwell progressed into car racing, driving for JHR Developments in the second half of the Ginetta Junior Championship. He made his single-seater debut in 2017 at Croft Circuit with Arden in the F4 British Championship, becoming the youngest ever participant in a British F4 race at fifteen years old. That same year, Caldwell also debuted in the ADAC Formula 4 Championship, driving for ADAC Berlin-Brandenburg e.V. in two weekends.
In 2018, Caldwell switched to Prema in ADAC Formula 4, finishing seventh with four podiums and one win at Oschersleben. He also joined Prema in the Italian F4 Championship, partnering Enzo Fittipaldi and Gianluca Petecof. After a disappointing opening weekend, he secured two podiums and a pole position in France, followed by three podiums at Monza. A dominant weekend at Vallelunga, where he won all three races after qualifying on pole, put him in contention for the championship. He ultimately finished third in the Italian F4 standings.
2019 saw Caldwell remain with Prema, progressing to the Formula Regional European Championship alongside Enzo Fittipaldi and Frederik Vesti. He initially won the second race at Le Castellet, but was later disqualified for a technical infringement. He achieved podium finishes at Vallelunga and all three races at the Hungaroring. A charging drive in Austria was halted by a faulty gearbox, costing him a potential win. Caldwell then won in Imola, dedicating the victory to the late Anthoine Hubert following Hubert’s death at Spa. He finished fifth in the championship.
At the 2019 Macau Grand Prix, Caldwell raced with Trident, qualifying 17th before being caught up in an incident during the qualifying race. Contact with Andreas Estner during the main race caused his retirement due to front wing and tyre damage.
In 2022, while competing in Formula 2 with Campos Racing, Caldwell received a total of twelve penalty points across multiple races, including a disqualification from the Spa round after accumulating too many infringements. He later apologised to his team for the incident.
At the end of 2018, Caldwell made his GT racing debut in the Gulf 12 Hours, winning the GT4 category driving a Mercedes for Bullitt Racing. In 2021, he debuted in the FIA World Endurance Championship with ARC Bratislava, finishing eleventh in the LMP2 class at the 8 Hours of Bahrain.
In 2024, Caldwell joined Algarve Pro Racing for his second season in the European Le Mans Series, partnering Matthias Kaiser and Alex Lynn. He achieved his first ELMS victory at Spa-Francorchamps, and a second at Silverstone. A collision at the season finale in Portimão resulted in a last-place finish, but the team finished second in the championship. He also competed in the Asian Le Mans Series with Algarve Pro, achieving multiple podiums and a race win at Dubai.
Caldwell remained at APR for the 2025 ELMS season, partnering Quinn and Lendoudis. The trio won at Spa-Francorchamps and Silverstone, leading the championship standings before a collision at Portimão resulted in a second-place finish in the championship.
At the start of 2026, Caldwell revealed that his racing plans had fallen through, leaving him without a seat. He remained connected to Algarve Pro by becoming a driver coach for the 2026 ELMS season.
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