Bruce Waddell

D'Alessandro/Waddell were assigned by Skate Canada to make their debut on the ISU Junior Grand Prix, with one assignment to the 2017 JGP Australia in Brisbane.[4] Placing sixth, Waddell commented that the international competition made them "more nervous than usual."[5] Competing at the 2018 Canadian Junior Championships, they placed eighth.

Given two assignments on the Junior Grand Prix, D'Alessandro/Waddell were fourth at the 2018 JGP Austria and sixth at the 2018 JGP Canada, the latter held in Richmond, British Columbia. Competing at the 2019 Canadian Junior Championships, they won the bronze medal.[6]

Again assigned to two events on the Junior Grand Prix, D'Alessandro/Waddell began the season at the 2019 JGP Latvia, where they placed fourth, missing the bronze medal by 0.68 points after sitting in third after the rhythm dance.[7] At their second event, the 2019 JGP Italy, they won the silver medal, the highest colour of medal won by a Canadian dance team on the Junior Grand Prix that season.[8] D'Alessandro commented afterward "seeing your name on the podium with the Canadian flag next to it is a pretty cool feeling."[3]

D'Alessandro/Waddell won the gold at the 2020 Skate Canada Challenge.[9] This would be their final domestic competition of the season, as they were assigned as part of the Canadian delegation to the 2020 Winter Youth Olympics in Lausanne, which both had had as a longtime goal.[3] Competing in the ice dance event in Lausanne, D'Alessandro/Waddell placed third in the rhythm dance despite encountering level issues on several elements.[10] These continued in the free dance, where they placed fifth, and dropped to fourth place overall, 0.91 points behind bronze medalists Wolfkostin/Chen. Waddell said after "there were a few technical errors but I definitely still had a blast." They subsequently won a bronze medal in the team event.[11]

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.[12] 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.[13]