Born in Kelso, Scotland, Ogilvie moved to Australia at the age of twenty. One of his reasons for leaving his homeland was his admiration of the writer Adam Lindsay Gordon and like Gordon, a great love for horses. When he arrived in Australia he found work as a drover, a breaker, and a musterer. He worked at Maroupe, located in South Australia as well as Belalie on the Warrego. It was during this time that he began writing, his poetry focusing on the Outback life and it's many adventures in an acclamatory, romantic verse. Ogilvie had many of his works published in the Mount Gambier Border Watch, the Australasian and the Bulletin. A couple of years before his return to Scotland in 1901 he published his most well known collection of verse in 1898. It is considered to be his best and most notable piece of work.
While all of his works were published in Australia, he never returned. After his return to Scotland he continued to write poems that concerned the Scottish borders. The well known poet, Hugh McDairmund, hailed his work as a triumph. Unfortunately, though he was successful in both countries, he died practically unknown and has become one of the more obscure poets of that era.