The team was based in Jacksonville, Florida playing at Durkee Field in 1938. They moved to Cleveland in 1939 and became the Cleveland Bears, playing their home games at Hardware Field. They returned to Jacksonville as the Red Caps in 1941 for two seasons, dropping out of the NAL in July 1942. After the war, the Red Caps apparently continued as an unaffiliated Negro league team playing at Durkee Field.
The Red Caps only played seven league games their first season, finishing 3-4. After transferring to Cleveland in 1939, the Bears (according to Negro leagues historian John Holway) had the best overall record in the NAL but were not awarded the pennant, finishing with a 22-4 record in league play. The Kansas City Monarchs finished with more victories, going 25-13, and, as per the tradition of the time, were thereby declared league champions. Later research shows the Bears with a 20-21 record in 1939, third in the NAL.
The Bears fell hard in 1940, finishing last in the league with a 6-16 record. Returning to Jacksonville, the Red Caps finished second from last with an 8-10 record in league play. They fared no better in 1942 season, going 2-6 before dropping from the league in July.