He began publishing poetry in the Toronto Globe in 1899, while still a student.

The Toronto Globe and Mail gave the production a favorable review.

The old Toronto Globe came promptly to their aid.

From 1889 to 1892 he worked for the Toronto Globe as an illustrator and artist.

The Toronto Globe called it the "greatest game of hockey ever played on Canadian ice, or any other."

After graduating, he started as a staff writer at the Toronto Globe where he would remain until 1918.

In 1930, he also worked again with the Toronto Globe.

From 1905 to 1910, Cowper worked for the Toronto Globe.

He made his views on the subject public in a letter to the Toronto Globe.

He became a reporter for the Toronto Globe and Mail.