Career
Originally from Victorian Football Association (VFA) club Williamstown, Caldwell made his debut for Street Kilda in the 1909 VFL season, playing eight games. Caldwell enlisted in the Australian Imperial Forces (AIF) at the beginning of World War I and was sent to Gallipoli. After being severely injured in the fighting at Gallipoli, Caldwell was evacuated to Malta where he died in a military hospital in Valletta on 26 July 1915.
Caldwell was the brother of South Melbourne football player Jim Caldwell.