Stroll's car racing debut came in the 2014 Florida Winter Series, a non-championship series organised by the Ferrari Driver Academy. He raced against future Formula One competitors Nicholas Latifi and Max Verstappen, and took two podium finishes as well as pole position at Homestead–Miami Speedway.
Stroll made his competitive car racing debut in the 2014 Italian F4 Championship, driving for Prema Powerteam. Despite missing the final round due to injury, Stroll emerged as series champion, taking seven race wins, thirteen podium finishes and five pole positions.