Career
Born in Scotland, Montgomerie was playing in Montreal by 1915 when he was part of the Montreal All Star team which lost to the Toronto All Stars during their annual inter-city clash. At that time, he played for Highlanders. When World War I began, Montgomerie entered the Canadian Army and was assigned to the 42nd Battalion.
After the war, he returned to Canada.
In 1924, Montgomerie moved south to join the New Bedford Whalers of the American Soccer League. He remained with the Whalers until the fall of 1931, aside from six games with the Fall River Marksmen in the spring of 1931.