Career
A left-winger noted for his pace, he played for Manchester United, Winsford United and Portuguese Vale in the 1930s
Caldwell played for Manchester United, (without making any first-team appearances) and Winsford United, and after a trial at Aston Villa joined Portuguese Vale in May 1935. He played one Second Division game for the club in the 1934-1935 season. He scored ten goals in 42 games in the 1935-1936 season, the first one of note being against former employers Manchester United at Old Trafford in a 7–2 defeat.
However he was limited to just 13 Third Division North games in the 1936-1937 season, scoring two goals, as he was struck down with injury.
However he featured just four times in the Third Division South in the 1938-1939 season, and left the club as World World War II approached.