Over 1,000 entries were made this year for the annual contest run by the magazine, which is sold to help homeless people.
Martin Wellstead, aged six, from Wimborne, Dorset, was named the winner for his drawing of a smiling snowman underneath the word “Joy!”.
He said: “I looked at last year’s winner and the winner from the year before, before deciding what to draw.
“I thought that you guys needed a snowman so that is what I wanted to give you this year. It took me about three hours to draw my cover.”
Big Issue editor Paul McNamee said: ”[The cover] lifts your spirits and makes you smile, simply and honestly. That feels very timely right now.”
The magazine is on sale from today [Monday 4 December].