 In January 1914, Callaway scored an impressive 129, and a duck in the second innings, in a New South Wales Colts v Victorian Colts match at the Melbourne Cricket Ground.At the beginning of the 1914–15 season, Callaway moved to Waverley where one of his team-mates was a young Alan Kippax.Callaway made his first class debut aged 18 for New South Wales against Queensland at the SCG in February 1915.