Winans served in the Indian Territory and Texas from 1891 to 1897; was a professor of military science and tactics, Michigan Military Academy, from 1897 to 1898; and served with a regiment in the Philippines from 1899 to 1900. He was with the Punitive Expedition in Mexico in 1916. During World War I, Winans commanded the 64th Brigade Infantry, 32d Division, 1st Army Corps, American Expeditionary Force.