Williamstown Caldwell played his junior football with
CYMS Football Association (CYMSFA) club Williamstown CYMS, Yarraville Juniors and Newport Juniors before commencing with Williamstown in the VFA in 1905. He played until 1908 and was a premiership player with
Victorian Football Association (VFA) club
Williamstown in 1907, the Club's first. He transferred to South Melbourne in 1909.
South Melbourne In his debut season (1909), South Melbourne reached the
Grand Final but Caldwell missed playing due to a nine-week suspension for striking Carlton's
George Bruce in the Preliminary Final. Almost a decade later, in
1918, as captain-coach, he led the club to victory in the
1918. By then, Caldwell was playing as a rover and had become a regular
Victorian interstate representative.
Footscray Cleared from South Melbourne on 12 May 1920, he played three matches for Footscray in the VFA — on 15 May, 22 May, and 29 May — before resigning as a player and moving on to coach "Footscray Diggers", in the
Victorian Junior Football Association; and, at least, by 31 July 1920, he was serving as captain-coach of Camperdown in the Corangamite Football Association.
Williamstown Caldwell returned to captain-coach Williamstown In 1921 and 1922, and led them to a premiership in the former season. This meant Caldwell had played in both of Williamstown's first two premiership teams. In total, Caldwell played 81 games for 'Town, is a member of the WFC Hall of Fame and was selected on a wing in the WFC Team-of-the-Century.
Perth Cleared from Williamstown on 25 April 1923, he captain-coached the Perth team in 1923 and 1924 "without much success"; and, in the second half of the 1923 season, "was disqualified for the [remainder of] the season for abusing a field-umpire".
Carlton On the resignation of
Carlton's captain-coach
Paddy O'Brien — who (later) went to play with Footscray in its first VFL season —
Ray Brew acted as coach for four matches. Caldwell (then in Perth) was appointed coached of Carlton for the remainder of the 1925 VFL season.
Rutherglen Although offered another year at Carlton in 1926, Caldwell took up a more lucrative offer, and was appointed captain-coach of the
Rutherglen Football Club in the
Ovens and Murray Football League. Caldwell resigned as coach of Rutherglen in July, 1926. Due to financial considerations, the Rutherglen club not only decided not to appoint a playing coach for the 1927 season, but also decided not to appoint a paid coach at all.
South Melbourne Caldwell was appointed South Melbourne coach for the
1929 VFL season; yet, despite the team's
(unexpected) victory against Richmond on 1 June 1929, much dissatisfaction was expressed about Caldwell's coaching, and Caldwell was invited to resign, which he did, on the following Tuesday (4 June 1929). ==Death==