Caldwell topped the New Zealand regional table in the 2014/15 season to win a place in the preliminary round of the 2016 BDO World Darts Championship.

In his World Championship debut he defeated Alan Soutar with a respectable 90 average and also went six darts into a perfect leg.

Caldwell hit nine 180's in a first round match at the Lakeside World Championships in 2016, which equaled the current record.

Caldwell won the inaugural televised New Zealand national Super league in 2015.

Caldwell is the only player to hit a 9 dart finish in a New Zealand ranking event in 2015.