They have won three medals on the ISU Junior Grand Prix series, including gold at the 2021 JGP Slovakia, and bronze in the 2020 Winter Youth Olympics team event.

D'Alessandro/Waddell were pre-novice champions at the 2016 Skate Canada Challenge and then won the novice title at the 2017 Canadian Championships.

[4] Making their international debut as a dance team, they placed fourth at the 2017 Bavarian Open in the advanced novice division.

[7] 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.

[10] 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.

[13] 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.

As well, in-person domestic competition was limited, as a result of which D'Alessandro/Waddell competed only once during the season at a virtually-held 2021 Skate Canada Challenge.

[22] Due to the pandemic, the 2022 World Junior Championships could not be held as scheduled in Sofia in early March and, as a result, were rescheduled for Tallinn in mid-April.

With Bashynska/Beaumont winning the bronze medal, it was the first time two Canadian dance teams had stood on the podium together at the World Junior Championships.

[26] On May 3, 2022, D'Alessandro and Waddell announced on their joint Instagram account that they would no longer be skating together, stating, "the time has come when we are excited to move on with new separate adventures.