Two teams competed in the 1944 Memorial Cup, with one team winning all four games of the series.
The George Richardson Memorial Trophy champions Oshawa Generals of the Ontario Hockey Association in Eastern Canada competed against the Abbott Cup champions Trail Smoke Eaters of the Western Kootenay Junior Hockey League in Western Canada. In a best-of-seven series, held at Maple Leaf Gardens in Toronto, Ontario, Oshawa won their 3rd Memorial Cup, defeating Trail 4 games to 0. 
Game 1: Oshawa 9-2 Trail Game 2: Oshawa 5-2 Trail Game 3: Oshawa 15-4 Trail Game 4: Oshawa 11-4 Trail The George Richardson Memorial Trophy champions Oshawa Generals of the Ontario Hockey Association in Eastern Canada competed against the Abbott Cup champions Trail Smoke Eaters of the Western Kootenay Junior Hockey League in Western Canada. 
