voted him as the team's best player of the 2013 season. He was given a similar honour by the Red Patch Boys. At the start of the 2014 season, Caldwell continued to be in the first team regular, playing in the centre–back position, as well as, resuming his captain duties for Toronto. He then played in 2014 Canadian Championship#Final both legs of the Canadian Championship finals against Montreal Impact, as the club lost 2–1 on aggregate. However along the way, Caldwell faced two suspensions, including being sent–off against Sporting Kansas City on 24 May 2014. By mid–July, however, he suffered a quad tear that saw him sidelined for a month. It wasn't until on 24 August 2014 when Caldwell returned to the starting line–up against Chicago Fire, only to suffer an injury and substituted in the 22nd minute, as Toronto drew 2–2. Following the match, it was announced that he was sidelined for several weeks, having failed to recover from a quad injury. It wasn't until on 21 September 2014 when Caldwell returned to the starting line–up against Chivas USA and helped the club keep a clean sheet, winning 3–0. Following his return, he started in the remaining six matches of the 2014 season for Toronto. At the end of the 2014 season, Caldwell went on to make twenty–four appearances in all competitions. Reflecting in the season, he tweeted his frustration but determined to help the club get back on track next season. Ahead of the 2015 season, Caldwell was demoted from team captain following the promotion to captain of designated player and American national team mainstay Michael Bradley. He made two appearances for Toronto before suffering an achilles tendon problems during a match against Columbus Crew on 14 March 2015. As a result, Caldwell was sidelined for a month. As a result of his injury, Caldwell announced his retirement from professional football on 14 July 2015. He retired four months after his brother, Gary. International career Youth Team In March 2000, Caldwell was called up to the Scotland U21 squad for the first time. He made his U21 debut, starting the whole game, in a 2–0 loss against France U21 on 28 March 2000. Caldwell then played alongside Gary for the first time for Scotland U21, as the U21 side lost 1–0 against Belgium U21. He later made three more appearances for Scotland U21 later in 2001. The next