Education
Born in Princeton, New Jersey, Caldwell attended Ivy League Princeton University, playing for the men"s soccer team, Princeton Tigers.
Born in Princeton, New Jersey, Caldwell attended Ivy League Princeton University, playing for the men"s soccer team, Princeton Tigers.
He represented Canada at under-20 and under-23 levels. He also played for Canadian Soccer League team Winnipeg Fury. Caldwell moved to England in 1995 to play for Football League club Colchester United.
He made six first-team appearances for the U"s between 1995 and 1998, making his debut in a Football League Trophy defeat to Swindon Town on 8 November 1995.
Caldwell left Colchester in 1998, returning to Canada to join up with Toronto Supra. He played five games for the under-20s in 1992, also featuring in the Paolo Valenti Trophy held in Italy.
Caldwell was later selected in the Canada under-23 team, featuring in the 1994 Pan American Games qualifying rounds and totalling another five appearances during the year.
At the age of 18, Caldwell was a member of the Canada under-20 team that finished in third place at the 1992 CONCACAF U-20 Tournament which was held in Canada. He was a member of the 1996 Olympic qualifying team, although he failed to make an appearance.