Kai Yip started boxing in 1954 at the age of 14 and competed in over 100 bouts during his career. In 1954, he claimed the Provincial Junior 100 lb. Boxing championship, and in 1955, he won both the 110 lb. title and the Golden Gloves. He was the Provincial Senior and Golden Glove 112 lb. Champion in 1956. That same year, he was the Canadian Champion in that class. Kai Yip won the Provincial Senior and Canadian Senior Championship in the 119 lb. class in 1958. He represented Canada at the British Empire Games in Wales.