When he was a young boy Jorge Guerra got a job delivering bread on a bicycle. From there Guerra joined the Chilean Cycling Club where he rode on the local velodrome, becoming a junior champion when he was 16. Two years later he competed in road races in Viña and Santiago, finishing second and third, respectively. As one of the best cyclists of his time in Chile, Guerra was selected to represent his nation in the road race at the 1936 Berlin Olympics. His best results came at the Chilean national road race championships, winning the race in 1938 and 1941. Guerra also had good results on the track, winning both the individual pursuit and points race at the Pan American Championships.