Skate Canada assigned D'Alessandro/Waddell to one of Canada's three berths at the 2020 World Junior Championships in Tallinn, Estonia, and also to compete at the 2020 Bavarian Open in the junior division. They won the bronze medal, narrowly behind fellow Canadians Bronsard/Bouaraguia. D'Alessandro/Waddell finished the season at the World Junior Championships, where they placed eleventh, narrowly behind the other Canadian teams competing, Bronsard/Bouraguia and Makita/Gunara.
