Cap Stubbs and Tippe by Edwina Dumm

From Wikipedia: Cap Stubbs and Tippie is a syndicated newspaper comic strip created by the cartoonist Edwina Dumm that ran for 48 years, from August 21, 1918, to September 3, 1966. The strip focused on a young boy, Joseph "Cap" Stubbs, and his dog, Tippie. The many adventures of Cap and Tippie led to the discomfort of his parents and his grandmother, Sara Bailey, who clearly doted on the boy despite the fact that his high energy and general boyishness constantly drove her to distraction. For more info: https://www.toonopedia.com/capstubs.htm