Glasgow joined the Wide Bay Regiment of the Queensland Mounted Infantry in 1893, and he was sent to London in 1897 as part of a small contingent of 20 personnel from Queensland to attend the Diamond Jubilee of Queen Victoria. In 1899, he volunteered for service in South Africa and was commissioned as a lieutenant, assigned to the 1st Queensland Mounted Infantry Contingent. While in South Africa, he took part in the relief of Kimberley, the fighting on the Modder, and the occupation of Bloemfontein. For his services, he was mentioned in despatches and awarded the Distinguished Service Order (DSO) in 1901.