Education
Caldwell, who was educated at Hamilton Grammar School, started playing football relatively late in childhood.
Caldwell, who was educated at Hamilton Grammar School, started playing football relatively late in childhood.
Caldwell has previously played for Hibernian, Alloa Athletic, Street Mirren, Greenock Morton and Ayr United. He played for various boys teams before joining the youth system of Edinburgh professional club Hibernian (Hibs). Hibs manager Pat Fenlon added Caldwell to the first team squad soon after he took charge in November 2011.
Caldwell was named as a substitute in a game against Motherwell, but was prevented from playing because the match was abandoned.
He made his senior debut on 10 December 2011, appearing as a substitute in a 2–0 defeat against Rangers. Caldwell agreed a new two-year contract with Hibs in March 2012.
Caldwell was mainly used as a substitute during the 2012-2013 season. In his second starting appearance for Hibs, he scored a match winning goal against Hearts at Tynecastle on 12 May 2013.
He made seven first team appearances in the early months of the 2013-2014 season, but did not play for Hibs after 30 November.
Caldwell was loaned to Alloa Athletic in January 2014 for the rest of the season. He scored a goal in his first appearance for Alloa, in a 3–1 defeat against Queen of the South. Caldwell went on trial with Street Mirren in July 2014 and subsequently signed a one-year contract with the club, with the option of a second year.
After limited appearances for the club, Caldwell terminated his contract by mutual consent on 9 January 2015.
In his time at the club, Caldwell made 15 appearances, scoring two goals. On the same day Caldwell left Street Mirren, he signed a contract with Scottish League One side Greenock Morton until the end of season 2014–2015.
He was released by Morton at the end of the season. In July 2015, Caldwell signed for Ayr United on a six-month deal.
At the start of January 2016, Caldwell was released by Ayr United having made 22 appearances, scoring five times for the side.
He subsequently signed for league rivals Cowdenbeath shortly after his released from Ayr. International
Caldwell was invited to a training camp of the Scotland national under-19 football team in March 2011.