[1][2][3] Cuylle did not think Peterborough was a good fit for him and he committed to play college hockey for Penn State University.

[2][4][6] In his first season with Windsor, Cuylle scored 26 goals, fourth in the OHL among 16-year-old players, and 15 assists for 41 points.

34 draft-eligible North American skater by the NHL Central Scouting Bureau after being ranked no.

[2][7] With the OHL shut down for the 2020–21 season due to the COVID-19 pandemic, Cuylle played in 18 games with the Rangers' American Hockey League (AHL) affiliate, the Hartford Wolf Pack, scoring two goals and three assists for a total of five points.

[25] Cuylle was selected to Canada's team in the 2022 World Junior Ice Hockey Championships.

According to Letowski, "He can find pockets in the offensive zone — those little, quiet areas — and if he gets it on a stick, especially in juniors, then he can just shoot it past goalies.

"[2] NHL director of Central Scouting Dan Marr said of Cuylle ahead of the 2020 draft "He brings more of that power-forward type of game and I thought he got away from that last year...He can own the corner, battle for position at the net and play to the strengths of his size and [use] it in a smart way.

"[10] Before the 2023–24 season, Rangers coach Peter Laviolette compared Cuylle to Wilson, who Laviolette had coached in Washington, saying "I don't know if you want to exactly make that comparison because he's a young kid that’s trying to make it to the NHL, but I do think that those are his traits.